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_1516792
_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, 2(C12 H12 O2)'
_chemical_formula_sum            'C34 H26 I2 N2 O8'
_chemical_formula_weight         844.37
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                82.120(2)
_cell_angle_beta                 80.651(3)
_cell_angle_gamma                79.408(2)
_cell_formula_units_Z            1
_cell_length_a                   6.6274(3)
_cell_length_b                   9.4654(3)
_cell_length_c                   12.3549(4)
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.311
_cell_measurement_theta_min      3.648
_cell_volume                     747.10(5)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.02
_diffrn_measured_fraction_theta_full 0.823
_diffrn_measured_fraction_theta_max 0.934
_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_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.823
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4204
_diffrn_reflns_point_group_measured_fraction_full 0.823
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.312
_diffrn_reflns_theta_min         3.648
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    17.033
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0432 before and 0.0222 after correction.
The Ratio of minimum to maximum transmission is 0.8334.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_description       Needle
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0209
_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^)+(0.0339P)^2^+0.7294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2108
_reflns_number_total             2217
_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               1516792
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.638
_shelx_estimated_absorpt_t_min   0.072
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C16(H16), C17(H17), C7(H7), C9(H9), C11(H11)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C6(H6A,H6B,H6C)
;