#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/77/2017720.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_2017720
loop_
_publ_author_name
'Abboud, Mohamed'
'Kadimi, Amal'
'Mamane, Victor'
'Aubert, Emmanuel'
_publ_section_title
;
 Conformational disorder in
 4-(5,5'-dibromo-2'-chloro-4,4'-bipyridyl-2-yl)benzaldehyde: role of
 π--π and halogen interactions
;
_journal_coeditor_code           KU3026
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o381
_journal_page_last               o384
_journal_paper_doi               10.1107/S0108270110024261
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H9 Br2 Cl N2 O'
_chemical_formula_moiety         'C17 H9 Br2 Cl N2 O'
_chemical_formula_sum            'C17 H9 Br2 Cl N2 O'
_chemical_formula_weight         452.53
_chemical_melting_point          170
_chemical_name_systematic
;
4-(5,5'-dibromo-2'-chloro-4,4'-bipyridyl-2-yl)benzaldehyde
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.082(2)
_cell_angle_beta                 94.473(2)
_cell_angle_gamma                104.401(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5759(2)
_cell_length_b                   8.4629(2)
_cell_length_c                   13.1534(2)
_cell_measurement_reflns_used    19163
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      37.6573
_cell_measurement_theta_min      3.2053
_cell_volume                     787.52(3)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'Mercury (Macrae et al.,  2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
;
'SIR2004 (Burla et al., 2005)'
;
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35546
_diffrn_reflns_theta_full        31.73
_diffrn_reflns_theta_max         31.73
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    5.324
_exptl_absorpt_correction_T_max  0.758
_exptl_absorpt_correction_T_min  0.444
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis Pro (Oxford Diffraction, 2009), based on expressions derived
by
Clark & Reid (1995)]
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2172
_exptl_crystal_size_mid          0.1539
_exptl_crystal_size_min          0.0649
_refine_diff_density_max         2.081
_refine_diff_density_min         -1.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0277
_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)+(0.0371P)²+0.6279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                4767
_reflns_number_total             5351
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ku3026.cif
_cod_data_source_block           I
_cod_database_code               2017720
_cod_database_fobs_code          2017720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br2 -0.21454(3) 0.40481(2) 0.630746(15) 0.02574(5) Uani d . 1 A 1
Br Br1 0.46231(2) 0.61723(2) 0.730990(15) 0.02387(5) Uani d . 1 A 1
Cl Cl1 0.35160(7) 0.07488(6) 0.39575(4) 0.02768(10) Uani d . 1 A 1
N N7 0.0487(2) 0.1677(2) 0.40743(13) 0.0261(3) Uani d . 1 A 1
C C10 0.1154(2) 0.2939(2) 0.62769(13) 0.0183(3) Uani d . 1 A 1
C C13 -0.0391(2) 0.2168(2) 0.97970(12) 0.0174(3) Uani d . 1 A 1
C C4 0.1519(2) 0.3497(2) 0.74460(13) 0.0174(3) Uani d . 1 A 1
C C16 -0.2482(3) 0.0428(2) 1.10670(14) 0.0226(3) Uani d . 1 A 1
C C8 0.1966(3) 0.1631(2) 0.46446(14) 0.0221(3) Uani d . 1 A 1
C C11 -0.0409(3) 0.3032(2) 0.56814(14) 0.0207(3) Uani d . 1 A 1
O O19A -0.3632(3) -0.0180(3) 1.26193(15) 0.0269(5) Uani d P 0.740(5) A 1
C C14 -0.0037(3) 0.2754(2) 1.08992(14) 0.0238(3) Uani d . 1 A 1
H H14 0.0925 0.3747 1.1220 0.029 Uiso calc R 1 A 1
C C2 0.0770(2) 0.3074(2) 0.91377(13) 0.0173(3) Uani d . 1 A 1
C C9 0.2390(3) 0.2212(2) 0.57369(13) 0.0205(3) Uani d . 1 A 1
H H9 0.3477 0.2118 0.6101 0.025 Uiso calc R 1 A 1
C C5 0.3030(2) 0.4799(2) 0.79958(14) 0.0193(3) Uani d . 1 A 1
C C3 0.0369(2) 0.2644(2) 0.80388(13) 0.0185(3) Uani d . 1 A 1
H H3 -0.0696 0.1764 0.7694 0.022 Uiso calc R 1 A 1
C C17 -0.2832(3) -0.0164(2) 0.99754(15) 0.0242(3) Uani d . 1 A 1
H H17 -0.3781 -0.1170 0.9660 0.029 Uiso calc R 1 A 1
N N1 0.2267(2) 0.4316(2) 0.96527(12) 0.0226(3) Uani d . 1 A 1
C C15 -0.1085(3) 0.1889(3) 1.15240(14) 0.0259(4) Uani d . 1 A 1
H H15 -0.0843 0.2300 1.2270 0.031 Uiso calc R 1 A 1
C C18 -0.1811(3) 0.0699(2) 0.93426(13) 0.0213(3) Uani d . 1 A 1
H H18 -0.2075 0.0292 0.8597 0.026 Uiso calc R 1 A 1
C C19A -0.3621(3) -0.0542(3) 1.17076(18) 0.0324(5) Uani d P 0.740(5) A 1
H H19A -0.4447 -0.1591 1.1329 0.039 Uiso calc PR 0.740(5) A 1
C C6 0.3346(3) 0.5154(2) 0.90908(15) 0.0245(3) Uani d . 1 A 1
H H6 0.4390 0.6043 0.9455 0.029 Uiso calc R 1 A 1
C C12 -0.0700(3) 0.2376(3) 0.45934(15) 0.0260(4) Uani d . 1 A 1
H H12 -0.1784 0.2424 0.4201 0.031 Uiso calc R 1 A 1
O O19B -0.4572(8) -0.1575(8) 1.1563(6) 0.0346(17) Uani d P 0.260(5) A 2
C C19B -0.3621(3) -0.0542(3) 1.17076(18) 0.0324(5) Uani d P 0.260(5) A 2
H H19B -0.3333 -0.0004 1.2440 0.039 Uiso calc PR 0.260(5) A 2
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N7 C12 . . 116.76(16) ?
C11 C10 C9 . . 117.62(16) ?
C11 C10 C4 . . 123.55(16) ?
C9 C10 C4 . . 118.77(15) ?
C18 C13 C14 . . 118.85(16) ?
C18 C13 C2 . . 121.24(14) ?
C14 C13 C2 . . 119.89(16) ?
C5 C4 C3 . . 117.14(15) ?
C5 C4 C10 . . 123.03(15) ?
C3 C4 C10 . . 119.75(15) ?
C15 C16 C17 . . 119.49(17) ?
C15 C16 C19A . . 122.10(18) ?
C17 C16 C19A . . 118.41(19) ?
N7 C8 C9 . . 125.78(18) ?
N7 C8 Cl1 . . 116.29(14) ?
C9 C8 Cl1 . . 117.93(15) ?
C12 C11 C10 . . 119.61(17) ?
C12 C11 Br2 . . 118.48(14) ?
C10 C11 Br2 . . 121.90(13) ?
C15 C14 C13 . . 120.31(18) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
N1 C2 C3 . . 121.39(16) ?
N1 C2 C13 . . 116.43(15) ?
C3 C2 C13 . . 122.17(15) ?
C8 C9 C10 . . 117.43(17) ?
C8 C9 H9 . . 121.3 ?
C10 C9 H9 . . 121.3 ?
C4 C5 C6 . . 119.23(16) ?
C4 C5 Br1 . . 122.13(13) ?
C6 C5 Br1 . . 118.59(13) ?
C4 C3 C2 . . 120.43(16) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C18 C17 C16 . . 120.63(18) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C6 N1 C2 . . 118.30(16) ?
C16 C15 C14 . . 120.45(17) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C17 C18 C13 . . 120.27(16) ?
C17 C18 H18 . . 119.9 ?
C13 C18 H18 . . 119.9 ?
O19A C19A C16 . . 128.3(3) ?
O19A C19A H19A . . 115.9 ?
C16 C19A H19A . . 115.9 ?
N1 C6 C5 . . 123.49(16) ?
N1 C6 H6 . . 118.3 ?
C5 C6 H6 . . 118.3 ?
N7 C12 C11 . . 122.76(18) ?
N7 C12 H12 . . 118.6 ?
C11 C12 H12 . . 118.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br2 C11 . 1.8864(19) ?
Br1 C5 . 1.8886(17) ?
Cl1 C8 . 1.7461(19) ?
N7 C8 . 1.313(3) ?
N7 C12 . 1.342(3) ?
C10 C11 . 1.397(2) ?
C10 C9 . 1.397(2) ?
C10 C4 . 1.485(2) ?
C13 C18 . 1.399(2) ?
C13 C14 . 1.403(2) ?
C13 C2 . 1.483(2) ?
C4 C5 . 1.390(2) ?
C4 C3 . 1.391(2) ?
C16 C15 . 1.387(3) ?
C16 C17 . 1.390(3) ?
C16 C19A . 1.484(3) ?
C8 C9 . 1.392(2) ?
C11 C12 . 1.391(3) ?
O19A C19A . 1.170(3) ?
C14 C15 . 1.388(3) ?
C14 H14 . 0.9500 ?
C2 N1 . 1.348(2) ?
C2 C3 . 1.397(2) ?
C9 H9 . 0.9500 ?
C5 C6 . 1.392(2) ?
C3 H3 . 0.9500 ?
C17 C18 . 1.386(2) ?
C17 H17 . 0.9500 ?
N1 C6 . 1.326(2) ?
C15 H15 . 0.9500 ?
C18 H18 . 0.9500 ?
C19A H19A . 0.9500 ?
C6 H6 . 0.9500 ?
C12 H12 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 C10 C4 C5 . . . . -117.6(2) ?
C9 C10 C4 C5 . . . . 65.3(2) ?
C11 C10 C4 C3 . . . . 65.7(2) ?
C9 C10 C4 C3 . . . . -111.39(19) ?
C12 N7 C8 C9 . . . . 1.3(3) ?
C12 N7 C8 Cl1 . . . . -179.03(14) ?
C9 C10 C11 C12 . . . . 1.4(3) ?
C4 C10 C11 C12 . . . . -175.67(17) ?
C9 C10 C11 Br2 . . . . -177.95(12) ?
C4 C10 C11 Br2 . . . . 4.9(2) ?
C18 C13 C14 C15 . . . . -0.2(3) ?
C2 C13 C14 C15 . . . . -178.30(17) ?
C18 C13 C2 N1 . . . . -170.15(17) ?
C14 C13 C2 N1 . . . . 7.9(2) ?
C18 C13 C2 C3 . . . . 8.3(3) ?
C14 C13 C2 C3 . . . . -173.66(17) ?
N7 C8 C9 C10 . . . . -1.3(3) ?
Cl1 C8 C9 C10 . . . . 179.02(13) ?
C11 C10 C9 C8 . . . . -0.2(2) ?
C4 C10 C9 C8 . . . . 177.10(15) ?
C3 C4 C5 C6 . . . . 1.7(3) ?
C10 C4 C5 C6 . . . . -175.03(17) ?
C3 C4 C5 Br1 . . . . -175.63(13) ?
C10 C4 C5 Br1 . . . . 7.6(2) ?
C5 C4 C3 C2 . . . . -1.5(3) ?
C10 C4 C3 C2 . . . . 175.32(16) ?
N1 C2 C3 C4 . . . . 0.0(3) ?
C13 C2 C3 C4 . . . . -178.32(16) ?
C15 C16 C17 C18 . . . . -0.6(3) ?
C19B C16 C17 C18 . . . . 179.83(18) ?
C3 C2 N1 C6 . . . . 1.3(3) ?
C13 C2 N1 C6 . . . . 179.75(16) ?
C17 C16 C15 C14 . . . . -0.2(3) ?
C19B C16 C15 C14 . . . . 179.37(18) ?
C13 C14 C15 C16 . . . . 0.6(3) ?
C16 C17 C18 C13 . . . . 1.0(3) ?
C14 C13 C18 C17 . . . . -0.6(3) ?
C2 C13 C18 C17 . . . . 177.49(17) ?
C15 C16 C19A O19A . . . . 7.0(3) ?
C17 C16 C19A O19A . . . . -173.5(2) ?
C2 N1 C6 C5 . . . . -1.1(3) ?
C4 C5 C6 N1 . . . . -0.4(3) ?
Br1 C5 C6 N1 . . . . 177.02(15) ?
C8 N7 C12 C11 . . . . 0.2(3) ?
C10 C11 C12 N7 . . . . -1.5(3) ?
Br2 C11 C12 N7 . . . . 177.89(15) ?
