#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516797.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_1516797
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 Cl2 N2 O4'
_chemical_formula_sum            'C10 H2 Cl2 N2 O4'
_chemical_formula_weight         285.04
_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                 90.693(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1051(12)
_cell_length_b                   5.4752(10)
_cell_length_c                   12.252(2)
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.872
_cell_measurement_theta_min      6.229
_cell_volume                     476.59(14)
_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 0.932
_diffrn_measured_fraction_theta_max 0.996
_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  0.0234
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2930
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.867
_diffrn_reflns_theta_min         6.229
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.271
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0480 before and 0.0331 after correction.
The Ratio of minimum to maximum transmission is 0.8738.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.105
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0313
_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)+(0.0443P)²+0.5603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                723
_reflns_number_total             807
_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_original_cell_volume        476.57(14)
_cod_database_code               1516797
#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   0.957
_shelx_estimated_absorpt_t_min   0.559
_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
Cl1 Cl 0.78766(8) 0.08424(11) 0.06287(5) 0.0160(2) Uani 1 1 d .
O1 O 0.0302(2) 0.6324(3) 0.13317(14) 0.0176(4) Uani 1 1 d .
O2 O 0.4226(3) -0.0134(3) 0.20328(14) 0.0189(4) Uani 1 1 d .
N1 N 0.1978(3) 0.2887(4) 0.18740(16) 0.0145(5) Uani 1 1 d .
H1 H 0.1189 0.2333 0.2364 0.017 Uiso 1 1 calc R
C1 C 0.6304(3) 0.3096(5) 0.02757(19) 0.0133(5) Uani 1 1 d .
C2 C 0.4570(3) 0.3330(5) 0.07881(19) 0.0114(5) Uani 1 1 d .
C3 C 0.3672(4) 0.1762(5) 0.1640(2) 0.0161(6) Uani 1 1 d .
C4 C 0.1650(4) 0.4966(5) 0.1261(2) 0.0148(6) Uani 1 1 d .
C5 C 0.3312(3) 0.5193(5) 0.05238(19) 0.0129(5) 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'
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'
Cl Cl 0.3639 0.7018 '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
C4 N1 C3 113.3(2) .
C2 C1 Cl1 121.9(2) .
C5 C1 Cl1 122.1(2) 3_665
C5 C1 C2 116.0(2) 3_665
C1 C2 C3 130.2(2) .
C5 C2 C1 122.0(2) .
C5 C2 C3 107.7(2) .
O2 C3 N1 125.4(2) .
O2 C3 C2 129.0(2) .
N1 C3 C2 105.5(2) .
O1 C4 N1 126.3(2) .
O1 C4 C5 128.2(2) .
N1 C4 C5 105.5(2) .
C1 C5 C2 121.9(2) 3_665
C1 C5 C4 130.2(2) 3_665
C2 C5 C4 107.9(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.717(3) .
O1 C4 1.217(3) .
O2 C3 1.208(3) .
N1 C3 1.385(3) .
N1 C4 1.381(3) .
C1 C2 1.395(4) .
C1 C5 1.385(4) 3_665
C2 C3 1.500(4) .
C2 C5 1.392(4) .
C4 C5 1.501(3) .
C5 C1 1.385(4) 3_665
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
Cl1 C1 C2 C3 -3.8(4) . .
Cl1 C1 C2 C5 178.29(19) . .
O1 C4 C5 C1 -2.8(5) . 3_665
O1 C4 C5 C2 175.4(2) . .
N1 C4 C5 C1 178.3(2) . 3_665
N1 C4 C5 C2 -3.5(3) . .
C1 C2 C3 O2 -4.0(4) . .
C1 C2 C3 N1 178.3(2) . .
C1 C2 C5 C1 1.0(4) . 3_665
C1 C2 C5 C4 -177.4(2) . .
C3 N1 C4 O1 -177.6(2) . .
C3 N1 C4 C5 1.3(3) . .
C3 C2 C5 C1 -177.4(2) . 3_665
C3 C2 C5 C4 4.3(3) . .
C4 N1 C3 O2 -176.5(2) . .
C4 N1 C3 C2 1.3(3) . .
C5 C1 C2 C3 177.0(2) 3_665 .
C5 C1 C2 C5 -0.9(4) 3_665 .
C5 C2 C3 O2 174.1(3) . .
C5 C2 C3 N1 -3.5(3) . .
