#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:28:31 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246058 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556797.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1556797
loop_
_publ_author_name
'Aakeröy, Christer B'
'Spartz, Christine L.'
'Dembowski, Sean'
'Dwyre, Savannah'
'Desper, John'
_publ_section_title
;
 A systematic structural study of halogen bonding versus hydrogen bonding
 within competitive supramolecular systems.
;
_journal_issue                   'Pt 5'
_journal_name_full               IUCrJ
_journal_page_first              498
_journal_page_last               510
_journal_paper_doi               10.1107/S2052252515010854
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety
;
(C7 H2 Br F4 N O)2 (C12 H10 N2)
;
_chemical_formula_sum            'C26 H14 Br2 F8 N4 O2'
_chemical_formula_weight         726.23
_chemical_name_systematic
;
SD-1--20-10--8 (4-Br---F4-PhCH=NOH,)2 1,2-bis(4-pyridyl)ethylene
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.537(2)
_cell_angle_beta                 96.861(2)
_cell_angle_gamma                93.060(2)
_cell_formula_units_Z            2
_cell_length_a                   5.8370(3)
_cell_length_b                   12.8464(5)
_cell_length_c                   18.1146(8)
_cell_measurement_reflns_used    9332
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      2.53
_cell_volume                     1306.46(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16525
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    4.781
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                3946
_reflns_number_total             4377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lc5065.cif
_cod_data_source_block           BrF4OX14
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/IUCr/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1556797
_publcif_datablock.id            {e3a6530c-99d8-4389-a453-d0124ad3871e}
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.75028(5) 0.54628(2) 0.104058(16) 0.04831(13) Uani 1 1 d .
Br2 Br 0.19535(5) 0.32794(2) 0.077187(15) 0.05174(13) Uani 1 1 d .
N11 N -0.4211(4) 1.02290(16) 0.20929(12) 0.0406(5) Uani 1 1 d .
C12 C -0.3903(4) 0.9554(2) 0.14305(14) 0.0392(5) Uani 1 1 d .
H12 H -0.2540 0.9181 0.1417 0.047 Uiso 1 1 calc R
C13 C -0.5456(4) 0.93735(18) 0.07698(14) 0.0359(5) Uani 1 1 d .
H13 H -0.5160 0.8881 0.0318 0.043 Uiso 1 1 calc R
C14 C -0.7462(4) 0.99140(17) 0.07641(13) 0.0326(5) Uani 1 1 d .
C17 C -0.9088(4) 0.97285(18) 0.00585(13) 0.0345(5) Uani 1 1 d .
H17 H -0.8812 0.9164 -0.0357 0.041 Uiso 1 1 calc R
C15 C -0.7782(4) 1.06249(18) 0.14535(13) 0.0368(5) Uani 1 1 d .
H15 H -0.9115 1.1018 0.1481 0.044 Uiso 1 1 calc R
C16 C -0.6162(4) 1.07467(18) 0.20842(13) 0.0375(5) Uani 1 1 d .
H16 H -0.6426 1.1226 0.2546 0.045 Uiso 1 1 calc R
N21 N 1.5188(4) 0.27315(15) 0.46759(11) 0.0394(5) Uani 1 1 d .
C22 C 1.4739(4) 0.16716(19) 0.43733(13) 0.0385(5) Uani 1 1 d .
H22 H 1.3302 0.1423 0.4058 0.046 Uiso 1 1 calc R
C23 C 1.6256(4) 0.09278(18) 0.44970(13) 0.0372(5) Uani 1 1 d .
H23 H 1.5860 0.0186 0.4269 0.045 Uiso 1 1 calc R
C24 C 1.8374(4) 0.12641(17) 0.49578(12) 0.0318(5) Uani 1 1 d .
C27 C 2.0087(4) 0.05321(17) 0.51359(12) 0.0335(5) Uani 1 1 d .
H27 H 2.1445 0.0845 0.5476 0.040 Uiso 1 1 calc R
C25 C 1.8837(4) 0.23595(18) 0.52677(13) 0.0364(5) Uani 1 1 d .
H25 H 2.0259 0.2630 0.5585 0.044 Uiso 1 1 calc R
C26 C 1.7225(4) 0.30590(18) 0.51140(14) 0.0391(5) Uani 1 1 d .
H26 H 1.7584 0.3807 0.5330 0.047 Uiso 1 1 calc R
C31 C 0.3041(4) 0.79216(17) 0.24647(13) 0.0327(5) Uani 1 1 d .
C32 C 0.2459(4) 0.75038(17) 0.16734(13) 0.0341(5) Uani 1 1 d .
F32 F 0.0609(3) 0.78066(11) 0.12896(8) 0.0434(3) Uani 1 1 d .
C33 C 0.3779(4) 0.67905(19) 0.12624(13) 0.0383(5) Uani 1 1 d .
F33 F 0.3118(3) 0.64353(13) 0.05016(8) 0.0524(4) Uani 1 1 d .
C34 C 0.5731(4) 0.64462(18) 0.16085(14) 0.0380(5) Uani 1 1 d .
C35 C 0.6335(4) 0.68451(19) 0.23865(15) 0.0381(5) Uani 1 1 d .
F35 F 0.8225(3) 0.65418(12) 0.27547(9) 0.0477(4) Uani 1 1 d .
C36 C 0.4991(4) 0.75520(17) 0.27997(13) 0.0352(5) Uani 1 1 d .
F36 F 0.5656(3) 0.79102(12) 0.35611(8) 0.0470(4) Uani 1 1 d .
C37 C 0.1788(4) 0.8733(2) 0.29382(13) 0.0387(5) Uani 1 1 d .
H37A H 0.2282 0.8969 0.3474 0.046 Uiso 1 1 calc R
N37 N 0.0060(4) 0.91189(16) 0.26405(11) 0.0390(5) Uani 1 1 d .
O37 O -0.0795(4) 0.99141(16) 0.31670(10) 0.0512(5) Uani 1 1 d .
H37 H -0.203(7) 1.008(3) 0.286(2) 0.077 Uiso 1 1 d .
C41 C 0.7318(4) 0.39586(16) 0.30186(12) 0.0304(5) Uani 1 1 d .
C42 C 0.7586(4) 0.31744(17) 0.23631(13) 0.0329(5) Uani 1 1 d .
F42 F 0.9425(3) 0.25940(11) 0.23486(8) 0.0465(4) Uani 1 1 d .
C43 C 0.6010(4) 0.29816(18) 0.17110(13) 0.0355(5) Uani 1 1 d .
F43 F 0.6400(3) 0.22264(12) 0.10957(8) 0.0489(4) Uani 1 1 d .
C44 C 0.4055(4) 0.35337(19) 0.16742(13) 0.0371(5) Uani 1 1 d .
C45 C 0.3753(4) 0.43112(19) 0.23210(14) 0.0359(5) Uani 1 1 d .
F45 F 0.1903(3) 0.48872(13) 0.23144(9) 0.0484(4) Uani 1 1 d .
C46 C 0.5364(4) 0.45122(17) 0.29692(13) 0.0327(5) Uani 1 1 d .
F46 F 0.5000(3) 0.53033(11) 0.35667(8) 0.0441(3) Uani 1 1 d .
C47 C 0.8949(4) 0.42297(17) 0.37339(13) 0.0342(5) Uani 1 1 d .
H47A H 0.8665 0.4802 0.4142 0.041 Uiso 1 1 calc R
N47 N 1.0732(3) 0.37169(14) 0.38198(11) 0.0352(4) Uani 1 1 d .
O47 O 1.1966(3) 0.41254(13) 0.45447(9) 0.0409(4) Uani 1 1 d .
H47 H 1.299(6) 0.371(3) 0.455(2) 0.061 Uiso 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'
F F 0.0727 0.0534 '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'
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
C12 N11 C16 116.2(2) . .
N11 C12 C13 123.5(2) . .
N11 C12 H12 118.2 . .
C13 C12 H12 118.2 . .
C12 C13 C14 120.0(2) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C13 C14 C15 116.7(2) . .
C13 C14 C17 119.6(2) . .
C15 C14 C17 123.7(2) . .
C17 C17 C14 126.3(3) 2_375 .
C17 C17 H17 116.9 2_375 .
C14 C17 H17 116.9 . .
C16 C15 C14 119.5(2) . .
C16 C15 H15 120.3 . .
C14 C15 H15 120.3 . .
N11 C16 C15 124.1(2) . .
N11 C16 H16 117.9 . .
C15 C16 H16 117.9 . .
C26 N21 C22 117.1(2) . .
N21 C22 C23 123.2(2) . .
N21 C22 H22 118.4 . .
C23 C22 H22 118.4 . .
C22 C23 C24 119.9(2) . .
C22 C23 H23 120.0 . .
C24 C23 H23 120.0 . .
C25 C24 C23 116.8(2) . .
C25 C24 C27 119.3(2) . .
C23 C24 C27 124.0(2) . .
C27 C27 C24 126.0(3) 2_956 .
C27 C27 C27 84.7(2) 2_956 2_756
C24 C27 C27 51.70(12) . 2_756
C27 C27 H27 117.0 2_956 .
C24 C27 H27 117.0 . .
C27 C27 H27 141.5 2_756 .
C26 C25 C24 120.0(2) . .
C26 C25 H25 120.0 . .
C24 C25 H25 120.0 . .
N21 C26 C25 123.0(2) . .
N21 C26 H26 118.5 . .
C25 C26 H26 118.5 . .
C36 C31 C32 115.7(2) . .
C36 C31 C37 119.5(2) . .
C32 C31 C37 124.7(2) . .
F32 C32 C33 117.7(2) . .
F32 C32 C31 120.8(2) . .
C33 C32 C31 121.5(2) . .
F33 C33 C32 117.9(2) . .
F33 C33 C34 120.5(2) . .
C32 C33 C34 121.6(2) . .
C35 C34 C33 117.9(2) . .
C35 C34 Br1 121.0(2) . .
C33 C34 Br1 121.14(19) . .
F35 C35 C34 120.5(2) . .
F35 C35 C36 119.1(2) . .
C34 C35 C36 120.4(2) . .
F36 C36 C35 117.8(2) . .
F36 C36 C31 119.3(2) . .
C35 C36 C31 122.9(2) . .
N37 C37 C31 120.8(2) . .
N37 C37 H37A 119.6 . .
C31 C37 H37A 119.6 . .
C37 N37 O37 112.31(19) . .
N37 O37 H37 100(2) . .
C46 C41 C42 115.8(2) . .
C46 C41 C47 119.18(19) . .
C42 C41 C47 125.0(2) . .
F42 C42 C43 117.69(19) . .
F42 C42 C41 120.7(2) . .
C43 C42 C41 121.6(2) . .
F43 C43 C42 118.4(2) . .
F43 C43 C44 119.8(2) . .
C42 C43 C44 121.8(2) . .
C43 C44 C45 117.4(2) . .
C43 C44 Br2 121.17(18) . .
C45 C44 Br2 121.43(19) . .
F45 C45 C46 119.5(2) . .
F45 C45 C44 120.0(2) . .
C46 C45 C44 120.5(2) . .
F46 C46 C45 117.3(2) . .
F46 C46 C41 119.8(2) . .
C45 C46 C41 122.9(2) . .
N47 C47 C41 121.70(19) . .
N47 C47 H47A 119.2 . .
C41 C47 H47A 119.2 . .
C47 N47 O47 110.20(18) . .
N47 O47 H47 102(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C34 1.873(2) .
Br2 C44 1.874(2) .
N11 C12 1.344(3) .
N11 C16 1.350(3) .
C12 C13 1.377(3) .
C12 H12 0.9500 .
C13 C14 1.393(3) .
C13 H13 0.9500 .
C14 C15 1.403(3) .
C14 C17 1.461(3) .
C17 C17 1.326(5) 2_375
C17 H17 0.9500 .
C15 C16 1.366(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
N21 C26 1.337(3) .
N21 C22 1.342(3) .
C22 C23 1.375(3) .
C22 H22 0.9500 .
C23 C24 1.393(3) .
C23 H23 0.9500 .
C24 C25 1.386(3) .
C24 C27 1.467(3) .
C27 C27 1.334(4) 2_956
C27 C27 11.720(5) 2_756
C27 H27 0.9500 .
C25 C26 1.384(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C36 1.385(3) .
C31 C32 1.401(3) .
C31 C37 1.473(3) .
C32 F32 1.339(3) .
C32 C33 1.371(4) .
C33 F33 1.348(3) .
C33 C34 1.379(4) .
C34 C35 1.377(4) .
C35 F35 1.344(3) .
C35 C36 1.378(4) .
C36 F36 1.349(3) .
C37 N37 1.266(3) .
C37 H37A 0.9500 .
N37 O37 1.384(3) .
O37 H37 0.92(4) .
C41 C46 1.381(3) .
C41 C42 1.397(3) .
C41 C47 1.471(3) .
C42 F42 1.338(3) .
C42 C43 1.372(3) .
C43 F43 1.347(3) .
C43 C44 1.379(4) .
C44 C45 1.386(3) .
C45 F45 1.342(3) .
C45 C46 1.377(3) .
C46 F46 1.346(3) .
C47 N47 1.274(3) .
C47 H47A 0.9500 .
N47 O47 1.389(2) .
O47 H47 0.82(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O37 H37 N11 0.92(4) 1.82(4) 2.730(3) 168(4)
O47 H47 N21 0.82(4) 1.88(4) 2.693(2) 173(3)
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_4
C16 N11 C12 C13 -0.4(3) .
N11 C12 C13 C14 0.7(4) .
C12 C13 C14 C15 -0.3(3) .
C12 C13 C14 C17 179.2(2) .
C13 C14 C17 C17 -171.6(3) 2_375
C15 C14 C17 C17 7.9(4) 2_375
C13 C14 C15 C16 -0.4(3) .
C17 C14 C15 C16 -179.9(2) .
C12 N11 C16 C15 -0.3(4) .
C14 C15 C16 N11 0.7(4) .
C26 N21 C22 C23 0.3(4) .
N21 C22 C23 C24 0.2(4) .
C22 C23 C24 C25 -0.4(3) .
C22 C23 C24 C27 178.8(2) .
C25 C24 C27 C27 -178.0(3) 2_956
C23 C24 C27 C27 2.9(5) 2_956
C25 C24 C27 C27 137.8(2) 2_756
C23 C24 C27 C27 -41.29(18) 2_756
C23 C24 C25 C26 0.1(3) .
C27 C24 C25 C26 -179.1(2) .
C22 N21 C26 C25 -0.6(4) .
C24 C25 C26 N21 0.4(4) .
C36 C31 C32 F32 -179.9(2) .
C37 C31 C32 F32 -2.1(3) .
C36 C31 C32 C33 -1.2(3) .
C37 C31 C32 C33 176.5(2) .
F32 C32 C33 F33 -0.5(3) .
C31 C32 C33 F33 -179.2(2) .
F32 C32 C33 C34 179.1(2) .
C31 C32 C33 C34 0.4(4) .
F33 C33 C34 C35 179.3(2) .
C32 C33 C34 C35 -0.3(4) .
F33 C33 C34 Br1 -0.9(3) .
C32 C33 C34 Br1 179.50(17) .
C33 C34 C35 F35 -179.7(2) .
Br1 C34 C35 F35 0.5(3) .
C33 C34 C35 C36 1.0(3) .
Br1 C34 C35 C36 -178.74(17) .
F35 C35 C36 F36 0.2(3) .
C34 C35 C36 F36 179.5(2) .
F35 C35 C36 C31 178.8(2) .
C34 C35 C36 C31 -2.0(4) .
C32 C31 C36 F36 -179.51(19) .
C37 C31 C36 F36 2.6(3) .
C32 C31 C36 C35 2.0(3) .
C37 C31 C36 C35 -175.9(2) .
C36 C31 C37 N37 176.9(2) .
C32 C31 C37 N37 -0.7(4) .
C31 C37 N37 O37 -176.3(2) .
C46 C41 C42 F42 179.7(2) .
C47 C41 C42 F42 0.3(3) .
C46 C41 C42 C43 0.8(3) .
C47 C41 C42 C43 -178.7(2) .
F42 C42 C43 F43 -0.2(3) .
C41 C42 C43 F43 178.8(2) .
F42 C42 C43 C44 179.5(2) .
C41 C42 C43 C44 -1.5(4) .
F43 C43 C44 C45 -179.2(2) .
C42 C43 C44 C45 1.1(3) .
F43 C43 C44 Br2 -1.6(3) .
C42 C43 C44 Br2 178.72(17) .
C43 C44 C45 F45 178.9(2) .
Br2 C44 C45 F45 1.3(3) .
C43 C44 C45 C46 0.0(3) .
Br2 C44 C45 C46 -177.61(17) .
F45 C45 C46 F46 -1.1(3) .
C44 C45 C46 F46 177.8(2) .
F45 C45 C46 C41 -179.6(2) .
C44 C45 C46 C41 -0.7(4) .
C42 C41 C46 F46 -178.1(2) .
C47 C41 C46 F46 1.4(3) .
C42 C41 C46 C45 0.4(3) .
C47 C41 C46 C45 179.8(2) .
C46 C41 C47 N47 177.3(2) .
C42 C41 C47 N47 -3.2(4) .
C41 C47 N47 O47 -179.61(19) .
