#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209545.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_7209545
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Panikkattu, Sheelu'
'Chopade, Prashant D.'
'Desper, John'
_publ_section_title
;
 Competing hydrogen-bond and halogen-bond donors in crystal engineering
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              3125
_journal_paper_doi               10.1039/c2ce26747k
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety
;
(C10 H8 N4) (C7 H2 Br F4 N O)2
;
_chemical_formula_sum            'C24 H12 Br2 F8 N6 O2'
_chemical_formula_weight         728.22
_chemical_name_common
;3,3'-AzoPy 5-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhCHO
oxime)2
;
_chemical_name_systematic
;
3,3'-AzoPy 5-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhCHO oxime)2
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.765(3)
_cell_angle_beta                 103.151(3)
_cell_angle_gamma                99.733(3)
_cell_formula_units_Z            1
_cell_length_a                   8.3500(8)
_cell_length_b                   8.3646(8)
_cell_length_c                   9.8996(10)
_cell_measurement_reflns_used    5691
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.29
_cell_measurement_theta_min      2.61
_cell_volume                     628.00(11)
_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      120(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.901
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10635
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         31.49
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    3.325
_exptl_absorpt_correction_T_max  0.8255
_exptl_absorpt_correction_T_min  0.4159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.155
_refine_diff_density_min         -1.442
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                3174
_reflns_number_total             3773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26747k.txt
_cod_data_source_block           3,3'-azpy:Ox-Br
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7209545
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 0.69484(3) 1.09011(3) 0.90003(3) 0.02597(12) Uani 1 1 d .
C11 C 0.6696(3) 0.6372(3) 0.4834(3) 0.0187(5) Uani 1 1 d .
C12 C 0.5453(3) 0.7296(3) 0.4859(3) 0.0200(5) Uani 1 1 d .
F12 F 0.4097(2) 0.6899(2) 0.36964(18) 0.0280(4) Uani 1 1 d .
C13 C 0.5542(3) 0.8624(3) 0.6080(3) 0.0216(5) Uani 1 1 d .
F13 F 0.4273(2) 0.9416(2) 0.60229(18) 0.0284(4) Uani 1 1 d .
C14 C 0.6875(3) 0.9127(3) 0.7349(3) 0.0203(5) Uani 1 1 d .
C15 C 0.8119(3) 0.8207(3) 0.7362(3) 0.0224(5) Uani 1 1 d .
F15 F 0.9424(2) 0.8600(2) 0.85587(18) 0.0293(4) Uani 1 1 d .
C16 C 0.8022(3) 0.6887(3) 0.6135(3) 0.0207(5) Uani 1 1 d .
F16 F 0.9270(2) 0.6049(2) 0.62079(19) 0.0293(4) Uani 1 1 d .
C17 C 0.6678(3) 0.4923(3) 0.3602(3) 0.0221(5) Uani 1 1 d .
H17A H 0.7564 0.4346 0.3694 0.026 Uiso 1 1 calc R
N17 N 0.5480(3) 0.4427(3) 0.2403(3) 0.0231(4) Uani 1 1 d .
O17 O 0.5707(3) 0.3020(3) 0.1405(2) 0.0269(4) Uani 1 1 d .
H17 H 0.492(5) 0.288(5) 0.079(4) 0.032 Uiso 1 1 d .
N21 N 0.2842(3) 0.2591(3) -0.0736(3) 0.0265(5) Uani 1 1 d .
C22 C 0.2229(3) 0.1320(4) -0.2009(3) 0.0250(5) Uani 1 1 d .
H22 H 0.2720 0.0365 -0.2143 0.030 Uiso 1 1 calc R
C23 C 0.0910(3) 0.1324(4) -0.3147(3) 0.0227(5) Uani 1 1 d .
N23 N 0.0465(3) -0.0109(3) -0.4453(3) 0.0240(5) Uani 1 1 d .
C24 C 0.0128(4) 0.2682(4) -0.2939(3) 0.0255(5) Uani 1 1 d .
H24 H -0.0795 0.2713 -0.3689 0.031 Uiso 1 1 calc R
C25 C 0.0736(4) 0.3980(4) -0.1609(3) 0.0278(6) Uani 1 1 d .
H25 H 0.0225 0.4918 -0.1425 0.033 Uiso 1 1 calc R
C26 C 0.2095(4) 0.3907(4) -0.0544(3) 0.0269(5) Uani 1 1 d .
H26 H 0.2517 0.4823 0.0358 0.032 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 0.0033 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'
F F 0.0171 0.0103 '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
C14 Br1 O17 158.49(9) . 1_566
C12 C11 C16 115.1(2) . .
C12 C11 C17 125.5(2) . .
C16 C11 C17 119.4(2) . .
F12 C12 C13 117.1(2) . .
F12 C12 C11 120.9(2) . .
C13 C12 C11 122.0(2) . .
F13 C13 C12 118.1(2) . .
F13 C13 C14 119.9(2) . .
C12 C13 C14 122.0(2) . .
C13 C14 C15 117.2(2) . .
C13 C14 Br1 121.19(18) . .
C15 C14 Br1 121.54(19) . .
F15 C15 C16 119.2(2) . .
F15 C15 C14 120.4(2) . .
C16 C15 C14 120.4(2) . .
F16 C16 C15 117.8(2) . .
F16 C16 C11 118.9(2) . .
C15 C16 C11 123.3(2) . .
N17 C17 C11 120.5(2) . .
N17 C17 H17A 119.7 . .
C11 C17 H17A 119.7 . .
C17 N17 O17 110.5(2) . .
N17 O17 H17 98(3) . .
C22 N21 C26 117.7(2) . .
N21 C22 C23 123.2(3) . .
N21 C22 H22 118.4 . .
C23 C22 H22 118.4 . .
C22 C23 C24 118.9(3) . .
C22 C23 N23 115.6(2) . .
C24 C23 N23 125.5(2) . .
N23 N23 C23 113.5(3) 2_554 .
C25 C24 C23 117.9(3) . .
C25 C24 H24 121.1 . .
C23 C24 H24 121.1 . .
C24 C25 C26 119.6(3) . .
C24 C25 H25 120.2 . .
C26 C25 H25 120.2 . .
N21 C26 C25 122.6(3) . .
N21 C26 H26 118.7 . .
C25 C26 H26 118.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C14 1.867(2) .
Br1 O17 3.0557(19) 1_566
C11 C12 1.396(3) .
C11 C16 1.400(3) .
C11 C17 1.462(4) .
C12 F12 1.338(3) .
C12 C13 1.379(4) .
C13 F13 1.340(3) .
C13 C14 1.383(4) .
C14 C15 1.393(3) .
C15 F15 1.334(3) .
C15 C16 1.377(4) .
C16 F16 1.350(3) .
C17 N17 1.278(3) .
C17 H17A 0.9500 .
N17 O17 1.387(3) .
O17 H17 0.76(4) .
N21 C22 1.332(4) .
N21 C26 1.345(4) .
C22 C23 1.386(4) .
C22 H22 0.9500 .
C23 C24 1.394(4) .
C23 N23 1.427(4) .
N23 N23 1.258(5) 2_554
C24 C25 1.379(4) .
C24 H24 0.9500 .
C25 C26 1.385(4) .
C25 H25 0.9500 .
C26 H26 0.9500 .
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
O17 H17 N21 0.76(4) 1.95(4) 2.708(3) 178(4)
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
C16 C11 C12 F12 -178.2(2) . .
C17 C11 C12 F12 -0.2(4) . .
C16 C11 C12 C13 0.4(4) . .
C17 C11 C12 C13 178.4(2) . .
F12 C12 C13 F13 0.3(4) . .
C11 C12 C13 F13 -178.4(2) . .
F12 C12 C13 C14 179.1(2) . .
C11 C12 C13 C14 0.5(4) . .
F13 C13 C14 C15 177.3(2) . .
C12 C13 C14 C15 -1.5(4) . .
F13 C13 C14 Br1 0.0(4) . .
C12 C13 C14 Br1 -178.8(2) . .
O17 Br1 C14 C13 47.4(4) 1_566 .
O17 Br1 C14 C15 -129.9(2) 1_566 .
C13 C14 C15 F15 -178.7(2) . .
Br1 C14 C15 F15 -1.4(4) . .
C13 C14 C15 C16 1.7(4) . .
Br1 C14 C15 C16 179.1(2) . .
F15 C15 C16 F16 0.0(4) . .
C14 C15 C16 F16 179.5(2) . .
F15 C15 C16 C11 179.5(2) . .
C14 C15 C16 C11 -0.9(4) . .
C12 C11 C16 F16 179.4(2) . .
C17 C11 C16 F16 1.3(4) . .
C12 C11 C16 C15 -0.1(4) . .
C17 C11 C16 C15 -178.3(2) . .
C12 C11 C17 N17 2.0(4) . .
C16 C11 C17 N17 179.9(3) . .
C11 C17 N17 O17 -178.8(2) . .
C26 N21 C22 C23 2.2(4) . .
N21 C22 C23 C24 -2.9(4) . .
N21 C22 C23 N23 177.5(3) . .
C22 C23 N23 N23 -165.6(3) . 2_554
C24 C23 N23 N23 14.8(4) . 2_554
C22 C23 C24 C25 1.3(4) . .
N23 C23 C24 C25 -179.1(3) . .
C23 C24 C25 C26 0.7(4) . .
C22 N21 C26 C25 0.0(4) . .
C24 C25 C26 N21 -1.5(4) . .
