The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts.
Raatikainen, Kari; Cametti, Massimo; Rissanen, Kari; Beilstein journal of organic chemistry 6 (2010) 4–; doi:10.3762/bjoc.6.4

data_4029791
_publ_section_title
;
 The subtle balance of weak supramolecular interactions: The hierarchy of
 halogen and hydrogen bonds in haloanilinium and halopyridinium salts.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              4
_journal_paper_doi               10.3762/bjoc.6.4
_journal_volume                  6
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C6 H7 I N, H2 O4 P'
_chemical_formula_sum            'C6 H9 I N O4 P'
_chemical_formula_weight         317.01
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-09-23T15:14:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.81190(10)
_cell_length_b                   9.8242(2)
_cell_length_c                   25.8681(5)
_cell_measurement_reflns_used    40034
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_measurement_wavelength     0.71073
_cell_volume                     1985.26(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.908266E-1
_diffrn_orient_matrix_UB_12      -0.714702E-1
_diffrn_orient_matrix_UB_13      -0.23104E-2
_diffrn_orient_matrix_UB_21      0.631604E-1
_diffrn_orient_matrix_UB_22      -0.565504E-1
_diffrn_orient_matrix_UB_23      0.258719E-1
_diffrn_orient_matrix_UB_31      -0.644034E-1
_diffrn_orient_matrix_UB_32      0.453338E-1
_diffrn_orient_matrix_UB_33      0.286308E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            24333
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.6
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    3.371
_exptl_absorpt_correction_T_max  0.4302
_exptl_absorpt_correction_T_min  0.2749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing et al., 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.025
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0120P)^2^+3.9613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0509
_reflns_number_gt                2140
_reflns_number_total             2271
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            1860-5397-6-4-S2.cif
_cod_data_source_block           6
_cod_database_code               4029791