#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:22:51 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209548.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_7209548
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) (C6 H F4 I O)
;
_chemical_formula_sum            'C16 H9 F4 I N4 O'
_chemical_formula_weight         476.17
_chemical_name_common
'4,4'-AzoPy 3-HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-I-F4-PhOH'
_chemical_name_systematic
;
4,4'-AzoPy 3-HBXB (4-pyridyl)-N=N-(4-pyridyl), 4-I-F4-PhOH
;
_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                81.558(3)
_cell_angle_beta                 85.932(3)
_cell_angle_gamma                78.342(3)
_cell_formula_units_Z            2
_cell_length_a                   6.1515(5)
_cell_length_b                   9.8197(7)
_cell_length_c                   13.7443(10)
_cell_measurement_reflns_used    7041
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      68.81
_cell_measurement_theta_min      3.25
_cell_volume                     803.57(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 0.944
_diffrn_measured_fraction_theta_max 0.926
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11713
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         68.90
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    16.211
_exptl_absorpt_correction_T_max  0.5633
_exptl_absorpt_correction_T_min  0.1813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0275
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                2604
_reflns_number_total             2764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26747k.txt
_cod_data_source_block           4,4'-azpy:OH-I
_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_cell_volume        803.57(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7209548
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
N11 N 0.2493(5) 0.2299(3) 0.4821(2) 0.0284(7) Uani 1 1 d .
C12 C 0.4327(6) 0.2858(4) 0.4668(3) 0.0290(8) Uani 1 1 d .
H12 H 0.4406 0.3644 0.4984 0.035 Uiso 1 1 calc R
C13 C 0.6116(6) 0.2330(4) 0.4065(3) 0.0277(8) Uani 1 1 d .
H13 H 0.7399 0.2742 0.3971 0.033 Uiso 1 1 calc R
C14 C 0.5982(6) 0.1194(4) 0.3605(3) 0.0244(7) Uani 1 1 d .
N14 N 0.7887(5) 0.0685(3) 0.3001(2) 0.0277(7) Uani 1 1 d .
C15 C 0.4094(6) 0.0601(4) 0.3757(3) 0.0271(8) Uani 1 1 d .
H15 H 0.3974 -0.0186 0.3451 0.032 Uiso 1 1 calc R
C16 C 0.2402(6) 0.1198(4) 0.4368(3) 0.0285(8) Uani 1 1 d .
H16 H 0.1101 0.0804 0.4472 0.034 Uiso 1 1 calc R
N21 N 1.2797(5) -0.1576(3) 0.0502(2) 0.0286(7) Uani 1 1 d .
C22 C 1.0968(7) -0.2132(4) 0.0654(3) 0.0322(8) Uani 1 1 d .
H22 H 1.0864 -0.2885 0.0309 0.039 Uiso 1 1 calc R
C23 C 0.9212(6) -0.1662(4) 0.1292(3) 0.0307(8) Uani 1 1 d .
H23 H 0.7934 -0.2080 0.1379 0.037 Uiso 1 1 calc R
C24 C 0.9375(6) -0.0574(4) 0.1794(3) 0.0255(7) Uani 1 1 d .
N24 N 0.7498(5) -0.0091(3) 0.2422(2) 0.0287(7) Uani 1 1 d .
C25 C 1.1243(6) 0.0022(4) 0.1646(3) 0.0289(8) Uani 1 1 d .
H25 H 1.1383 0.0777 0.1982 0.035 Uiso 1 1 calc R
C26 C 1.2908(6) -0.0514(4) 0.0992(3) 0.0284(8) Uani 1 1 d .
H26 H 1.4194 -0.0106 0.0887 0.034 Uiso 1 1 calc R
C31 C -0.1787(6) 0.3604(4) 0.6561(3) 0.0256(7) Uani 1 1 d .
O31 O -0.1160(4) 0.2688(3) 0.59237(19) 0.0332(6) Uani 1 1 d .
H31 H 0.0095 0.2775 0.5669 0.040 Uiso 1 1 calc R
C32 C -0.3758(6) 0.3560(4) 0.7129(3) 0.0261(8) Uani 1 1 d .
F32 F -0.4956(3) 0.2599(2) 0.70107(16) 0.0322(5) Uani 1 1 d .
C33 C -0.4498(6) 0.4466(4) 0.7805(3) 0.0260(7) Uani 1 1 d .
F33 F -0.6408(3) 0.4346(2) 0.83189(16) 0.0317(5) Uani 1 1 d .
C34 C -0.3321(6) 0.5474(4) 0.7975(3) 0.0250(7) Uani 1 1 d .
I1 I -0.45160(4) 0.68106(2) 0.902714(15) 0.02822(11) Uani 1 1 d .
C35 C -0.1384(6) 0.5524(4) 0.7416(3) 0.0267(8) Uani 1 1 d .
F35 F -0.0159(4) 0.6498(2) 0.75150(16) 0.0334(5) Uani 1 1 d .
C36 C -0.0647(6) 0.4637(4) 0.6734(3) 0.0274(8) Uani 1 1 d .
F36 F 0.1252(3) 0.4751(2) 0.61837(17) 0.0343(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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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_3
C16 N11 C12 118.1(3) .
N11 C12 C13 122.4(4) .
N11 C12 H12 118.8 .
C13 C12 H12 118.8 .
C14 C13 C12 118.4(3) .
C14 C13 H13 120.8 .
C12 C13 H13 120.8 .
C13 C14 C15 119.9(3) .
C13 C14 N14 115.9(3) .
C15 C14 N14 124.2(3) .
N24 N14 C14 113.2(3) .
C16 C15 C14 117.6(3) .
C16 C15 H15 121.2 .
C14 C15 H15 121.2 .
N11 C16 C15 123.6(3) .
N11 C16 H16 118.2 .
C15 C16 H16 118.2 .
C26 N21 C22 117.4(3) .
N21 C22 C23 123.3(4) .
N21 C22 H22 118.4 .
C23 C22 H22 118.4 .
C24 C23 C22 118.1(4) .
C24 C23 H23 120.9 .
C22 C23 H23 120.9 .
C23 C24 C25 119.7(4) .
C23 C24 N24 116.4(3) .
C25 C24 N24 123.8(3) .
N14 N24 C24 113.7(3) .
C24 C25 C26 118.0(3) .
C24 C25 H25 121.0 .
C26 C25 H25 121.0 .
N21 C26 C25 123.4(3) .
N21 C26 H26 118.3 .
C25 C26 H26 118.3 .
O31 C31 C32 118.8(3) .
O31 C31 C36 126.1(3) .
C32 C31 C36 115.1(3) .
C31 O31 H31 109.5 .
F32 C32 C33 119.1(3) .
F32 C32 C31 119.0(3) .
C33 C32 C31 121.9(3) .
F33 C33 C32 117.9(3) .
F33 C33 C34 120.1(3) .
C32 C33 C34 122.0(3) .
C35 C34 C33 116.2(3) .
C35 C34 I1 123.5(3) .
C33 C34 I1 120.3(3) .
C34 I1 N21 165.98(11) 1_366
F35 C35 C36 117.6(3) .
F35 C35 C34 120.3(3) .
C36 C35 C34 122.1(3) .
F36 C36 C35 119.8(3) .
F36 C36 C31 117.6(3) .
C35 C36 C31 122.6(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.337(5) .
N11 C12 1.342(5) .
C12 C13 1.391(6) .
C12 H12 0.9500 .
C13 C14 1.379(5) .
C13 H13 0.9500 .
C14 C15 1.391(5) .
C14 N14 1.435(5) .
N14 N24 1.245(4) .
C15 C16 1.381(5) .
C15 H15 0.9500 .
C16 H16 0.9500 .
N21 C26 1.337(5) .
N21 C22 1.337(5) .
C22 C23 1.390(6) .
C22 H22 0.9500 .
C23 C24 1.378(6) .
C23 H23 0.9500 .
C24 C25 1.382(5) .
C24 N24 1.435(5) .
C25 C26 1.387(5) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 O31 1.330(4) .
C31 C32 1.399(5) .
C31 C36 1.400(5) .
O31 H31 0.8400 .
C32 F32 1.343(4) .
C32 C33 1.372(5) .
C33 F33 1.344(4) .
C33 C34 1.393(5) .
C34 C35 1.377(5) .
C34 I1 2.090(4) .
I1 N21 2.960(3) 1_366
C35 F35 1.358(4) .
C35 C36 1.365(5) .
C36 F36 1.361(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
O31 H31 N11 0.84 1.84 2.614(4) 152.3
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 -0.3(5) .
N11 C12 C13 C14 0.3(6) .
C12 C13 C14 C15 -0.4(5) .
C12 C13 C14 N14 -179.3(3) .
C13 C14 N14 N24 -163.3(3) .
C15 C14 N14 N24 17.8(5) .
C13 C14 C15 C16 0.4(5) .
N14 C14 C15 C16 179.3(3) .
C12 N11 C16 C15 0.4(5) .
C14 C15 C16 N11 -0.4(5) .
C26 N21 C22 C23 -0.2(6) .
N21 C22 C23 C24 -0.3(6) .
C22 C23 C24 C25 0.6(6) .
C22 C23 C24 N24 178.1(3) .
C14 N14 N24 C24 178.3(3) .
C23 C24 N24 N14 166.4(3) .
C25 C24 N24 N14 -16.2(5) .
C23 C24 C25 C26 -0.4(5) .
N24 C24 C25 C26 -177.7(3) .
C22 N21 C26 C25 0.4(5) .
C24 C25 C26 N21 -0.1(6) .
O31 C31 C32 F32 -0.1(5) .
C36 C31 C32 F32 -179.9(3) .
O31 C31 C32 C33 179.6(3) .
C36 C31 C32 C33 -0.2(5) .
F32 C32 C33 F33 -0.2(5) .
C31 C32 C33 F33 -179.9(3) .
F32 C32 C33 C34 179.0(3) .
C31 C32 C33 C34 -0.7(5) .
F33 C33 C34 C35 -179.9(3) .
C32 C33 C34 C35 0.8(5) .
F33 C33 C34 I1 -0.1(4) .
C32 C33 C34 I1 -179.3(3) .
C35 C34 I1 N21 167.9(3) 1_366
C33 C34 I1 N21 -12.0(6) 1_366
C33 C34 C35 F35 178.3(3) .
I1 C34 C35 F35 -1.5(5) .
C33 C34 C35 C36 -0.1(5) .
I1 C34 C35 C36 -179.9(3) .
F35 C35 C36 F36 0.0(5) .
C34 C35 C36 F36 178.4(3) .
F35 C35 C36 C31 -179.3(3) .
C34 C35 C36 C31 -0.8(6) .
O31 C31 C36 F36 1.9(5) .
C32 C31 C36 F36 -178.3(3) .
O31 C31 C36 C35 -178.8(3) .
C32 C31 C36 C35 1.0(5) .
