#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516792.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_1516792
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         'C10 H2 I2 N2 O4, 2(C12 H12 O2)'
_chemical_formula_sum            'C34 H26 I2 N2 O8'
_chemical_formula_weight         844.37
_chemical_name_systematic
;
 ?
;
_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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0339P)²+0.7294P] where P=(Fo²+2Fc²)/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 > 2σ(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
#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   0.638
_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)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
I1 I 0.39792(3) 0.87949(2) 0.78287(2) 0.01481(9) Uani 1 1 d .
O1 O 0.6692(4) 0.7692(2) 0.26226(19) 0.0218(6) Uani 1 1 d .
O2 O 0.5434(4) 0.6082(2) 0.62837(19) 0.0189(5) Uani 1 1 d .
N1 N 0.6188(5) 0.6563(3) 0.4397(2) 0.0145(6) Uani 1 1 d .
H1 H 0.6510 0.5663 0.4239 0.017 Uiso 1 1 calc R
C1 C 0.6227(5) 0.7747(3) 0.3598(3) 0.0132(7) Uani 1 1 d .
C2 C 0.5601(5) 0.6924(3) 0.5457(3) 0.0127(7) Uani 1 1 d .
C3 C 0.5611(5) 0.9046(3) 0.4231(3) 0.0095(6) Uani 1 1 d .
C4 C 0.5228(5) 0.8551(3) 0.5350(3) 0.0095(6) Uani 1 1 d .
C5 C 0.4615(5) 0.9497(3) 0.6156(3) 0.0091(6) Uani 1 1 d .
O5 O 0.2554(4) 0.6004(3) 0.07027(19) 0.0207(5) Uani 1 1 d .
C12 C 0.4300(6) 0.5913(4) 0.1254(3) 0.0260(9) Uani 1 1 d .
H12A H 0.5312 0.6455 0.0793 0.039 Uiso 1 1 calc GR
H12B H 0.4935 0.4897 0.1394 0.039 Uiso 1 1 calc GR
H12C H 0.3857 0.6324 0.1958 0.039 Uiso 1 1 calc GR
C13 C 0.1508(6) 0.7361(4) 0.0426(3) 0.0178(8) Uani 1 1 d .
C14 C 0.2108(6) 0.8632(4) 0.0574(3) 0.0175(7) Uani 1 1 d .
H14 H 0.3327 0.8607 0.0894 0.021 Uiso 1 1 calc R
C15 C 0.0898(6) 0.9980(4) 0.0247(3) 0.0159(7) Uani 1 1 d .
C16 C 0.1461(6) 1.1322(4) 0.0376(3) 0.0182(8) Uani 1 1 d .
H16 H 0.2678 1.1323 0.0688 0.022 Uiso 1 1 calc R
C17 C 0.0287(6) 1.2602(4) 0.0058(3) 0.0178(8) Uani 1 1 d .
H17 H 0.0683 1.3483 0.0164 0.021 Uiso 1 1 calc R
O3 O 0.0662(4) 0.5925(2) 0.61255(18) 0.0149(5) Uani 1 1 d .
C6 C 0.0175(6) 0.5732(4) 0.7310(3) 0.0202(8) Uani 1 1 d .
H6A H -0.1270 0.6165 0.7528 0.030 Uiso 1 1 calc GR
H6B H 0.1092 0.6203 0.7637 0.030 Uiso 1 1 calc GR
H6C H 0.0373 0.4697 0.7570 0.030 Uiso 1 1 calc GR
C7 C 0.0916(5) 0.7457(3) 0.4466(3) 0.0124(7) Uani 1 1 d .
H7 H 0.1306 0.6613 0.4094 0.015 Uiso 1 1 calc R
C8 C 0.0460(5) 0.7327(3) 0.5629(3) 0.0109(7) Uani 1 1 d .
C9 C -0.0116(5) 0.8526(3) 0.6185(3) 0.0101(6) Uani 1 1 d .
H9 H -0.0432 0.8425 0.6967 0.012 Uiso 1 1 calc R
C10 C -0.0238(5) 0.9929(3) 0.5580(3) 0.0099(6) Uani 1 1 d .
C11 C -0.0798(5) 1.1203(3) 0.6125(3) 0.0119(7) Uani 1 1 d .
H11 H -0.1093 1.1123 0.6907 0.014 Uiso 1 1 calc R
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'
I I -0.3257 6.8362 '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
C1 N1 H1 123.0 . .
C2 N1 H1 123.0 . .
C2 N1 C1 114.0(3) . .
O1 C1 N1 125.6(3) . .
O1 C1 C3 129.5(3) . .
N1 C1 C3 105.0(3) . .
O2 C2 N1 125.9(3) . .
O2 C2 C4 128.7(3) . .
N1 C2 C4 105.4(3) . .
C4 C3 C1 107.9(3) . .
C5 C3 C1 129.5(3) 2_676 .
C5 C3 C4 122.6(3) 2_676 .
C3 C4 C2 107.8(3) . .
C5 C4 C2 130.3(3) . .
C5 C4 C3 121.9(3) . .
C3 C5 I1 121.7(2) 2_676 .
C3 C5 C4 115.5(3) 2_676 .
C4 C5 I1 122.9(2) . .
C13 O5 C12 116.9(3) . .
O5 C12 H12A 109.5 . .
O5 C12 H12B 109.5 . .
O5 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O5 C13 C14 124.9(3) . .
O5 C13 C17 115.0(3) . 2_575
C14 C13 C17 120.1(3) . 2_575
C13 C14 H14 120.1 . .
C13 C14 C15 119.8(3) . .
C15 C14 H14 120.1 . .
C14 C15 C16 121.9(3) . .
C15 C15 C14 120.2(4) 2_575 .
C15 C15 C16 117.9(4) 2_575 .
C15 C16 H16 119.4 . .
C17 C16 C15 121.2(3) . .
C17 C16 H16 119.4 . .
C13 C17 H17 119.6 2_575 .
C16 C17 C13 120.8(3) . 2_575
C16 C17 H17 119.6 . .
C8 O3 C6 116.7(2) . .
O3 C6 H6A 109.5 . .
O3 C6 H6B 109.5 . .
O3 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 H7 120.0 . .
C11 C7 H7 120.0 2_576 .
C11 C7 C8 120.1(3) 2_576 .
O3 C8 C7 114.5(3) . .
C9 C8 O3 124.5(3) . .
C9 C8 C7 121.0(3) . .
C8 C9 H9 120.3 . .
C8 C9 C10 119.5(3) . .
C10 C9 H9 120.3 . .
C10 C10 C9 120.0(3) 2_576 .
C10 C10 C11 118.7(4) 2_576 .
C11 C10 C9 121.3(3) . .
C7 C11 C10 120.7(3) 2_576 .
C7 C11 H11 119.6 2_576 .
C10 C11 H11 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C5 2.082(3) .
O1 C1 1.201(4) .
O2 C2 1.210(4) .
N1 H1 0.8800 .
N1 C1 1.389(4) .
N1 C2 1.375(4) .
C1 C3 1.505(4) .
C2 C4 1.505(4) .
C3 C4 1.396(4) .
C3 C5 1.385(4) 2_676
C4 C5 1.392(4) .
C5 C3 1.385(4) 2_676
O5 C12 1.419(5) .
O5 C13 1.370(4) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.378(5) .
C13 C17 1.408(6) 2_575
C14 H14 0.9500 .
C14 C15 1.422(5) .
C15 C15 1.416(8) 2_575
C15 C16 1.423(5) .
C16 H16 0.9500 .
C16 C17 1.360(5) .
C17 C13 1.408(6) 2_575
C17 H17 0.9500 .
O3 C6 1.440(4) .
O3 C8 1.375(4) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7 0.9500 .
C7 C8 1.412(5) .
C7 C11 1.371(5) 2_576
C8 C9 1.370(4) .
C9 H9 0.9500 .
C9 C10 1.427(4) .
C10 C10 1.410(6) 2_576
C10 C11 1.422(4) .
C11 C7 1.371(5) 2_576
C11 H11 0.9500 .
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
O1 C1 C3 C4 -179.7(4) . .
O1 C1 C3 C5 1.4(6) . 2_676
O2 C2 C4 C3 -179.7(3) . .
O2 C2 C4 C5 0.3(6) . .
N1 C1 C3 C4 -0.7(4) . .
N1 C1 C3 C5 -179.5(3) . 2_676
N1 C2 C4 C3 0.3(4) . .
N1 C2 C4 C5 -179.7(3) . .
C1 N1 C2 O2 179.2(3) . .
C1 N1 C2 C4 -0.8(4) . .
C1 C3 C4 C2 0.2(4) . .
C1 C3 C4 C5 -179.7(3) . .
C2 N1 C1 O1 180.0(3) . .
C2 N1 C1 C3 0.9(4) . .
C2 C4 C5 I1 -1.1(5) . .
C2 C4 C5 C3 -179.2(3) . 2_676
C3 C4 C5 I1 178.8(2) . .
C3 C4 C5 C3 0.7(5) . 2_676
C5 C3 C4 C2 179.2(3) 2_676 .
C5 C3 C4 C5 -0.8(5) 2_676 .
O5 C13 C14 C15 179.6(3) . .
C12 O5 C13 C14 4.7(5) . .
C12 O5 C13 C17 -176.2(3) . 2_575
C13 C14 C15 C15 -1.1(6) . 2_575
C13 C14 C15 C16 -179.5(3) . .
C14 C15 C16 C17 180.0(3) . .
C15 C15 C16 C17 1.5(6) 2_575 .
C15 C16 C17 C13 -1.1(5) . 2_575
C17 C13 C14 C15 0.6(5) 2_575 .
O3 C8 C9 C10 178.9(3) . .
C6 O3 C8 C7 -178.8(3) . .
C6 O3 C8 C9 1.7(5) . .
C7 C8 C9 C10 -0.6(5) . .
C8 C9 C10 C10 -0.1(6) . 2_576
C8 C9 C10 C11 -179.0(3) . .
C9 C10 C11 C7 -179.8(3) . 2_576
C10 C10 C11 C7 1.4(6) 2_576 2_576
C11 C7 C8 O3 -179.2(3) 2_576 .
C11 C7 C8 C9 0.4(5) 2_576 .
