#------------------------------------------------------------------------------
#$Date: 2019-05-13 10:49:06 +0300 (Mon, 13 May 2019) $
#$Revision: 215051 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/67/1516793.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1516793
loop_
_publ_author_name
'Cao, Dennis'
'Hong, Michael'
'Blackburn, Anthea K.'
'Liu, Zhichang'
'Holcroft, James M.'
'Stoddart, J. Fraser'
_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
_chemical_name_systematic
;
 ?
;
_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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0275P)²+1.3166P] where P=(Fo²+2Fc²)/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 > 2σ(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_sum            'C56 H56 Br4 N8 O16'
_cod_original_formula_weight         1416.72
_cod_original_formula_moiety         '2(C18 H26 N2 O4), 2(C10 H2 Br2 N2 O4)'
_cod_original_formula_units_Z            1
_cod_database_code               1516793
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
N2 N 0.9638(2) 0.61258(7) 0.31134(17) 0.0199(3) Uani 1 1 d .
H2 H 0.9678 0.6364 0.3882 0.024 Uiso 1 1 calc R
O3 O 1.1337(2) 0.71944(6) 0.28192(15) 0.0231(3) Uani 1 1 d .
O4 O 1.5323(2) 0.76506(6) 0.36935(16) 0.0262(3) Uani 1 1 d .
H4 H 1.5637 0.7848 0.2995 0.039 Uiso 1 1 calc GR
C6 C 1.0545(3) 0.54842(8) 0.7540(2) 0.0185(4) Uani 1 1 d .
H6 H 1.0735 0.5752 0.8359 0.022 Uiso 1 1 calc R
C7 C 1.0252(3) 0.57013(8) 0.6110(2) 0.0172(4) Uani 1 1 d .
H7 H 1.0221 0.6115 0.5947 0.021 Uiso 1 1 calc R
C8 C 0.9994(3) 0.53097(8) 0.4871(2) 0.0155(4) Uani 1 1 d .
C9 C 0.9705(3) 0.55232(8) 0.3355(2) 0.0163(4) Uani 1 1 d .
C10 C 0.9431(3) 0.51238(8) 0.2180(2) 0.0180(4) Uani 1 1 d .
H10 H 0.9226 0.5263 0.1178 0.022 Uiso 1 1 calc R
C11 C 0.9503(3) 0.63798(9) 0.1631(2) 0.0214(4) Uani 1 1 d .
H11A H 0.8235 0.6252 0.0962 0.026 Uiso 1 1 calc R
H11B H 1.0653 0.6244 0.1197 0.026 Uiso 1 1 calc R
C12 C 0.9543(3) 0.70457(9) 0.1773(2) 0.0232(4) Uani 1 1 d .
H12A H 0.9550 0.7230 0.0790 0.028 Uiso 1 1 calc R
H12B H 0.8339 0.7186 0.2134 0.028 Uiso 1 1 calc R
C13 C 1.1697(3) 0.78111(8) 0.2965(2) 0.0245(4) Uani 1 1 d .
H13A H 1.0543 0.8009 0.3278 0.029 Uiso 1 1 calc R
H13B H 1.1852 0.7979 0.1993 0.029 Uiso 1 1 calc R
C14 C 1.3590(3) 0.79081(8) 0.4119(2) 0.0271(4) Uani 1 1 d .
H14A H 1.3815 0.8337 0.4272 0.033 Uiso 1 1 calc R
H14B H 1.3418 0.7735 0.5083 0.033 Uiso 1 1 calc R
Br1 Br 0.42675(3) 0.45733(2) 0.14584(2) 0.01589(8) Uani 1 1 d .
O1 O 0.5760(2) 0.65687(6) 0.64717(15) 0.0245(3) Uani 1 1 d .
O2 O 0.4619(2) 0.59910(6) 0.15811(14) 0.0219(3) Uani 1 1 d .
N1 N 0.5162(2) 0.64170(7) 0.39291(18) 0.0190(3) Uani 1 1 d .
H1 H 0.5181 0.6788 0.3651 0.023 Uiso 1 1 calc R
C1 C 0.4650(2) 0.48147(8) 0.34611(19) 0.0128(3) Uani 1 1 d .
C2 C 0.4894(3) 0.54049(7) 0.3873(2) 0.0128(3) Uani 1 1 d .
C3 C 0.5234(2) 0.55839(8) 0.53685(19) 0.0129(3) Uani 1 1 d .
C4 C 0.5429(3) 0.62422(8) 0.5396(2) 0.0168(4) Uani 1 1 d .
C5 C 0.4859(3) 0.59492(8) 0.2928(2) 0.0162(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C9 N2 H2 118.9 . .
C9 N2 C11 122.22(16) . .
C11 N2 H2 118.9 . .
C13 O3 C12 113.74(15) . .
C14 O4 H4 109.5 . .
C7 C6 H6 119.3 . .
C7 C6 C10 121.36(17) . 3_766
C10 C6 H6 119.3 3_766 .
C6 C7 H7 119.9 . .
C6 C7 C8 120.26(17) . .
C8 C7 H7 119.9 . .
C7 C8 C8 119.3(2) . 3_766
C7 C8 C9 121.65(17) . .
C8 C8 C9 119.1(2) 3_766 .
N2 C9 C8 118.61(16) . .
N2 C9 C10 121.79(17) . .
C10 C9 C8 119.56(17) . .
C6 C10 H10 119.8 3_766 .
C9 C10 C6 120.47(18) . 3_766
C9 C10 H10 119.8 . .
N2 C11 H11A 110.0 . .
N2 C11 H11B 110.0 . .
N2 C11 C12 108.58(15) . .
H11A C11 H11B 108.4 . .
C12 C11 H11A 110.0 . .
C12 C11 H11B 110.0 . .
O3 C12 C11 106.92(15) . .
O3 C12 H12A 110.3 . .
O3 C12 H12B 110.3 . .
C11 C12 H12A 110.3 . .
C11 C12 H12B 110.3 . .
H12A C12 H12B 108.6 . .
O3 C13 H13A 110.0 . .
O3 C13 H13B 110.0 . .
O3 C13 C14 108.42(16) . .
H13A C13 H13B 108.4 . .
C14 C13 H13A 110.0 . .
C14 C13 H13B 110.0 . .
O4 C14 C13 112.32(16) . .
O4 C14 H14A 109.1 . .
O4 C14 H14B 109.1 . .
C13 C14 H14A 109.1 . .
C13 C14 H14B 109.1 . .
H14A C14 H14B 107.9 . .
C4 N1 H1 123.4 . .
C4 N1 C5 113.20(15) . .
C5 N1 H1 123.4 . .
C2 C1 Br1 121.99(13) . .
C3 C1 Br1 122.29(13) 3_666 .
C3 C1 C2 115.69(16) 3_666 .
C1 C2 C3 122.03(16) . .
C1 C2 C5 130.40(16) . .
C3 C2 C5 107.56(15) . .
C1 C3 C2 122.27(16) 3_666 .
C1 C3 C4 130.11(16) 3_666 .
C2 C3 C4 107.61(15) . .
O1 C4 N1 125.36(17) . .
O1 C4 C3 128.53(17) . .
N1 C4 C3 106.11(15) . .
O2 C5 N1 125.46(17) . .
O2 C5 C2 129.05(17) . .
N1 C5 C2 105.50(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 H2 0.8800 .
N2 C9 1.383(2) .
N2 C11 1.454(2) .
O3 C12 1.424(2) .
O3 C13 1.420(2) .
O4 H4 0.8400 .
O4 C14 1.431(3) .
C6 H6 0.9500 .
C6 C7 1.370(3) .
C6 C10 1.401(3) 3_766
C7 H7 0.9500 .
C7 C8 1.419(3) .
C8 C8 1.423(4) 3_766
C8 C9 1.439(3) .
C9 C10 1.386(3) .
C10 C6 1.401(3) 3_766
C10 H10 0.9500 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.515(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.500(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
Br1 C1 1.8731(17) .
O1 C4 1.213(2) .
O2 C5 1.209(2) .
N1 H1 0.8800 .
N1 C4 1.371(2) .
N1 C5 1.387(2) .
C1 C2 1.390(2) .
C1 C3 1.388(2) 3_666
C2 C3 1.396(3) .
C2 C5 1.502(2) .
C3 C1 1.388(2) 3_666
C3 C4 1.498(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N2 C9 C10 C6 -178.34(17) . 3_766
N2 C11 C12 O3 56.03(19) . .
O3 C13 C14 O4 62.0(2) . .
C6 C7 C8 C8 1.1(3) . 3_766
C6 C7 C8 C9 -179.32(17) . .
C7 C8 C9 N2 -1.4(3) . .
C7 C8 C9 C10 -179.11(16) . .
C8 C8 C9 N2 178.2(2) 3_766 .
C8 C8 C9 C10 0.5(3) 3_766 .
C8 C9 C10 C6 -0.7(3) . 3_766
C9 N2 C11 C12 -177.81(16) . .
C10 C6 C7 C8 -0.9(3) 3_766 .
C11 N2 C9 C8 175.30(16) . .
C11 N2 C9 C10 -7.0(3) . .
C12 O3 C13 C14 178.65(15) . .
C13 O3 C12 C11 174.14(16) . .
Br1 C1 C2 C3 -178.25(13) . .
Br1 C1 C2 C5 1.9(3) . .
C1 C2 C3 C1 0.0(3) . 3_666
C1 C2 C3 C4 179.82(16) . .
C1 C2 C5 O2 -0.5(3) . .
C1 C2 C5 N1 179.33(18) . .
C1 C3 C4 O1 1.0(3) 3_666 .
C1 C3 C4 N1 -179.18(17) 3_666 .
C2 C3 C4 O1 -178.80(18) . .
C2 C3 C4 N1 1.02(19) . .
C3 C1 C2 C3 0.0(3) 3_666 .
C3 C1 C2 C5 -179.88(17) 3_666 .
C3 C2 C5 O2 179.62(18) . .
C3 C2 C5 N1 -0.56(19) . .
C4 N1 C5 O2 -178.89(17) . .
C4 N1 C5 C2 1.3(2) . .
C5 N1 C4 O1 178.37(18) . .
C5 N1 C4 C3 -1.5(2) . .
C5 C2 C3 C1 179.91(15) . 3_666
C5 C2 C3 C4 -0.27(19) . .
