Two-point halogen bonding between 3,6-dihalopyromellitic diimides
Cao, Dennis; Hong, Michael; Blackburn, Anthea K.; Liu, Zhichang; Holcroft, James M.; Stoddart, J. Fraser; Chem. Sci. 5 (2014) 4242–; doi:10.1039/C4SC00999A

data_1516795
_publ_section_title
;
 Two-point halogen bonding between 3,6-dihalopyromellitic diimides
;
_journal_issue                   11
_journal_name_full               'Chem. Sci.'
_journal_page_first              4242
_journal_paper_doi               10.1039/C4SC00999A
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C10 H2 I2 N2 O4, C5 H9 N O, H2 O'
_chemical_formula_sum            'C15 H13 I2 N3 O6'
_chemical_formula_weight         585.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2014-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                93.245(3)
_cell_angle_beta                 102.205(3)
_cell_angle_gamma                99.769(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2221(5)
_cell_length_b                   9.4868(7)
_cell_length_c                   13.2822(9)
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.970
_cell_measurement_theta_min      3.421
_cell_volume                     872.51(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14244
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.010
_diffrn_reflns_theta_min         3.420
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    28.676
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0905 before and 0.0436 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1174 before and 0.0503 after correction.
 The Ratio of minimum to maximum transmission is 0.56.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 14075 reflections, Rint = 0.0463
 (10782 with I > 3sig(I), Rint = 0.0448)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.227
_exptl_crystal_description       needle
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.022
_exptl_transmission_factor_max   0.753015
_exptl_transmission_factor_min   0.418991
_refine_diff_density_max         1.742
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0556P)^2^+7.2499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2863
_reflns_number_total             3131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc00999a1.cif
_cod_data_source_block           p-1
_cod_depositor_comments
'Adding full bibliography for 1516792--1516797.cif.'
_cod_database_code               1516795
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.571
_shelx_estimated_absorpt_t_min   0.148
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB), C4S(H4SA,H4SB), C1S(H1SA,H1SB)
2.b Idealised Me refined as rotating group:
 C5S(H5SA,H5SB,H5SC)
;
_shelx_res_checksum              90046
_shelx_hkl_checksum              48532