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_1516793
_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         'C18 H26 N2 O4, C10 H2 Br2 N2 O4'
_chemical_formula_sum            'C28 H28 Br2 N4 O8'
_chemical_formula_weight         708.36
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2839 for OlexSys, GUI svn.r4720)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.623(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7598(4)
_cell_length_b                   22.6656(13)
_cell_length_c                   9.1153(5)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.085
_cell_measurement_theta_min      5.325
_cell_volume                     1367.96(14)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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      99.99
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13777
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.079
_diffrn_reflns_theta_min         5.325
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.278
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0363 after correction.
The Ratio of minimum to maximum transmission is 0.7195.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_description       Needle
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.061
_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     191
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+1.3166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0576
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2444
_reflns_number_total             2462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4sc00999a1.cif
_cod_data_source_block           p21c
_cod_depositor_comments
;
Adding full bibliography for 1516792--1516797.cif.

2019-05-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C18 H26 N2 O4), 2(C10 H2 Br2 N2 O4)'
_cod_original_formula_sum        'C56 H56 Br4 N8 O16'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1416.72
_cod_database_code               1516793
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.768
_shelx_estimated_absorpt_t_min   0.434
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C10(H10), N1(H1)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              66805
_shelx_hkl_checksum              41834