#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516796.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_1516796
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 Br2 N2 O4'
_chemical_formula_sum            'C10 H2 Br2 N2 O4'
_chemical_formula_weight         373.96
_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             2013-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2853 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.257(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3668(2)
_cell_length_b                   5.4181(2)
_cell_length_c                   12.5250(4)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.490
_cell_measurement_theta_min      3.256
_cell_volume                     499.54(3)
_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      99.9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17489
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.540
_diffrn_reflns_theta_min         2.767
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.122
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0724 after correction.
The Ratio of minimum to maximum transmission is 0.7455.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.486
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0216
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0239P)²+0.6474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1422
_reflns_number_total             1527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4sc00999a1.cif
_cod_data_source_block           p21-c
_cod_depositor_comments
'Adding full bibliography for 1516792--1516797.cif.'
_cod_database_code               1516796
#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   0.668
_shelx_estimated_absorpt_t_min   0.260
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
#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
Br1 Br 0.79294(2) 0.07105(4) 0.43300(2) 0.01288(7) Uani 1 1 d .
O1 O 0.4206(2) -0.0073(3) 0.29383(13) 0.0170(3) Uani 1 1 d .
O2 O 0.03946(19) 0.6343(3) 0.36386(12) 0.0162(3) Uani 1 1 d .
N1 N 0.1995(2) 0.2903(3) 0.31154(13) 0.0139(3) Uani 1 1 d .
H1 H 0.1198 0.2331 0.2636 0.017 Uiso 1 1 calc R
C1 C 0.6652(2) 0.4786(4) 0.55396(14) 0.0100(3) Uani 1 1 d .
C2 C 0.6258(2) 0.3114(3) 0.47208(14) 0.0100(3) Uani 1 1 d .
C3 C 0.4570(2) 0.3363(3) 0.41959(14) 0.0097(3) Uani 1 1 d .
C4 C 0.3671(2) 0.1802(4) 0.33402(15) 0.0125(3) Uani 1 1 d .
C5 C 0.1709(2) 0.4979(4) 0.37199(15) 0.0123(3) 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 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C5 N1 C4 113.16(15) . .
C2 C1 C3 121.66(16) . 3_666
C2 C1 C5 130.68(17) . 3_666
C3 C1 C5 107.65(16) 3_666 3_666
C1 C2 Br1 121.72(13) . .
C3 C2 Br1 121.98(14) . .
C3 C2 C1 116.29(16) . .
C1 C3 C4 107.72(15) 3_666 .
C2 C3 C1 122.04(16) . 3_666
C2 C3 C4 130.17(17) . .
O1 C4 N1 125.36(18) . .
O1 C4 C3 129.14(17) . .
N1 C4 C3 105.45(16) . .
O2 C5 N1 125.99(18) . .
O2 C5 C1 128.17(19) . 3_666
N1 C5 C1 105.83(16) . 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.8707(18) .
O1 C4 1.207(3) .
O2 C5 1.219(2) .
N1 C4 1.390(2) .
N1 C5 1.377(3) .
C1 C2 1.390(3) .
C1 C3 1.397(2) 3_666
C1 C5 1.498(3) 3_666
C2 C3 1.390(2) .
C3 C1 1.397(2) 3_666
C3 C4 1.499(3) .
C5 C1 1.498(3) 3_666
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
Br1 C2 C3 C1 -177.56(14) . 3_666
Br1 C2 C3 C4 5.7(3) . .
C1 C2 C3 C1 1.1(3) . 3_666
C1 C2 C3 C4 -175.57(18) . .
C1 C3 C4 O1 -174.7(2) 3_666 .
C1 C3 C4 N1 2.7(2) 3_666 .
C2 C3 C4 O1 2.4(3) . .
C2 C3 C4 N1 179.78(19) . .
C3 C1 C2 Br1 177.57(14) 3_666 .
C3 C1 C2 C3 -1.1(3) 3_666 .
C4 N1 C5 O2 176.1(2) . .
C4 N1 C5 C1 -2.7(2) . 3_666
C5 N1 C4 O1 177.6(2) . .
C5 N1 C4 C3 0.1(2) . .
C5 C1 C2 Br1 -3.0(3) 3_666 .
C5 C1 C2 C3 178.33(18) 3_666 .
