Hexamethylenetetramine is a fourfold acceptor of O—H···N hydrogen bonds in its 1:2 adduct with 2,2'-biphenol
MacLean, Elizabeth J.; Glidewell, Christopher; Ferguson, George; Gregson, Richard M.; Lough, Alan J.; Acta Crystallographica Section C 55 (1999) 1867–1870; doi:10.1107/S0108270199010422

data_2009201
_publ_section_title
;
 Hexamethylenetetramine is a fourfold acceptor of
 O---H&#x00B7;&#x00B7;&#x00B7;N hydrogen bonds in its 1:2 adduct with
 2,2'-biphenol
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1867
_journal_page_last               1870
_journal_paper_doi               10.1107/S0108270199010422
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C6 H12 N4, 2C12 H10 O2'
_chemical_formula_sum            'C30 H32 N4 O4'
_chemical_formula_weight         512.60
_chemical_name_systematic
;
Hexamethylenetetramine--2,2'-biphenol (1/2)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.199(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7615(9)
_cell_length_b                   13.0362(12)
_cell_length_c                   9.7878(9)
_cell_measurement_reflns_used    6608
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.02
_cell_volume                     1245.5(2)
_computing_cell_refinement       'LSCELL (Clegg, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        'SAINT (Siemens, 1994)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material
'SHELXL97 and WordPerfect macro PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997c)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source
'Daresbury, SRS station 9.8 (Cernik et al., 1997)'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68880
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12298
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         29.42
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997a)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details
'Flack (1983), 3625 reflections + 2983 Friedel equivalents'
_refine_ls_abs_structure_Flack   -0.6(13)
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997b)'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         6608
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.066
_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^)+(0.0348P)^2^+1.2638P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.144
_reflns_number_gt                5905
_reflns_number_total             6608
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1324.cif
_cod_data_source_block           9919
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2009201
_cod_database_fobs_code          2009201