#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209542.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_7209542
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)2
;
_chemical_formula_sum            'C22 H10 F8 I2 N4 O2'
_chemical_formula_weight         768.14
_chemical_name_common
'3,3'-AzoPy-3HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-PhOH)2'
_chemical_name_systematic
;
3,3'-AzoPy-3HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-PhOH)2
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.198(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0228(11)
_cell_length_b                   16.8636(10)
_cell_length_c                   7.2425(4)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.61
_cell_measurement_theta_min      2.42
_cell_volume                     2319.7(2)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18196
_diffrn_reflns_theta_full        32.02
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    2.806
_exptl_absorpt_correction_T_max  0.8497
_exptl_absorpt_correction_T_min  0.4671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0176
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0250P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0450
_refine_ls_wR_factor_ref         0.0463
_reflns_number_gt                3666
_reflns_number_total             3957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26747k.txt
_cod_data_source_block           3,3'-azpy:OH-I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      C2/c
_cod_database_code               7209542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N11 N 0.44861(6) 0.26401(7) 0.55097(17) 0.0216(2) Uani 1 1 d .
C12 C 0.44090(7) 0.34283(7) 0.5576(2) 0.0195(2) Uani 1 1 d .
H12 H 0.3979 0.3638 0.5973 0.023 Uiso 1 1 calc R
C13 C 0.49313(7) 0.39534(8) 0.50890(18) 0.0184(2) Uani 1 1 d .
N13 N 0.47662(6) 0.47739(7) 0.52716(16) 0.0198(2) Uani 1 1 d .
C14 C 0.55644(7) 0.36519(9) 0.45002(19) 0.0216(2) Uani 1 1 d .
H14 H 0.5931 0.3996 0.4159 0.026 Uiso 1 1 calc R
C15 C 0.56431(7) 0.28374(9) 0.4428(2) 0.0242(3) Uani 1 1 d .
H15 H 0.6067 0.2611 0.4033 0.029 Uiso 1 1 calc R
C16 C 0.50959(8) 0.23532(9) 0.4939(2) 0.0243(3) Uani 1 1 d .
H16 H 0.5156 0.1795 0.4883 0.029 Uiso 1 1 calc R
C21 C 0.32212(7) 0.12053(7) 0.67850(19) 0.0186(2) Uani 1 1 d .
O21 O 0.33728(6) 0.19765(6) 0.68085(16) 0.0238(2) Uani 1 1 d .
H21 H 0.3780(11) 0.2086(12) 0.627(3) 0.029 Uiso 1 1 d .
C22 C 0.37099(7) 0.05998(8) 0.6571(2) 0.0215(2) Uani 1 1 d .
F22 F 0.43823(5) 0.07968(6) 0.63190(17) 0.0352(2) Uani 1 1 d .
C23 C 0.35208(7) -0.01913(8) 0.6614(2) 0.0213(2) Uani 1 1 d .
F23 F 0.40230(5) -0.07411(5) 0.64176(16) 0.0333(2) Uani 1 1 d .
C24 C 0.28337(7) -0.04213(7) 0.68760(18) 0.0183(2) Uani 1 1 d .
I1 I 0.253716(5) -0.160260(5) 0.706907(12) 0.02132(4) Uani 1 1 d .
C25 C 0.23438(7) 0.01777(8) 0.70671(18) 0.0187(2) Uani 1 1 d .
F25 F 0.16685(4) -0.00032(5) 0.73284(15) 0.02822(19) Uani 1 1 d .
C26 C 0.25292(6) 0.09683(8) 0.70167(18) 0.0182(2) Uani 1 1 d .
F26 F 0.20304(5) 0.15228(5) 0.71769(14) 0.02464(18) 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 0.0033 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'
I I -0.4742 1.8119 '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 117.84(12) . .
N11 C12 C13 122.81(12) . .
N11 C12 H12 118.6 . .
C13 C12 H12 118.6 . .
C12 C13 C14 119.09(12) . .
C12 C13 N13 115.46(11) . .
C14 C13 N13 125.44(12) . .
N13 N13 C13 113.45(14) 5_666 .
C15 C14 C13 118.06(12) . .
C15 C14 H14 121.0 . .
C13 C14 H14 121.0 . .
C14 C15 C16 119.30(13) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
N11 C16 C15 122.90(13) . .
N11 C16 H16 118.6 . .
C15 C16 H16 118.6 . .
O21 C21 C26 118.90(12) . .
O21 C21 C22 124.81(12) . .
C26 C21 C22 116.28(11) . .
C21 O21 H21 112.6(13) . .
F22 C22 C23 119.50(12) . .
F22 C22 C21 118.63(11) . .
C23 C22 C21 121.86(12) . .
F23 C23 C22 118.41(12) . .
F23 C23 C24 120.15(12) . .
C22 C23 C24 121.43(12) . .
C25 C24 C23 116.98(12) . .
C25 C24 I1 120.36(10) . .
C23 C24 I1 122.62(9) . .
C24 I1 O21 156.81(4) . 4_546
F25 C25 C26 118.08(11) . .
F25 C25 C24 120.11(11) . .
C26 C25 C24 121.81(12) . .
F26 C26 C25 119.20(11) . .
F26 C26 C21 119.17(11) . .
C25 C26 C21 121.62(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.3384(17) .
N11 C16 1.3430(18) .
C12 C13 1.3911(18) .
C12 H12 0.9500 .
C13 C14 1.3958(18) .
C13 N13 1.4265(17) .
N13 N13 1.252(2) 5_666
C14 C15 1.383(2) .
C14 H14 0.9500 .
C15 C16 1.389(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 O21 1.3319(16) .
C21 C26 1.3947(17) .
C21 C22 1.3954(18) .
O21 H21 0.90(2) .
C22 F22 1.3439(15) .
C22 C23 1.3824(18) .
C23 F23 1.3446(15) .
C23 C24 1.3866(18) .
C24 C25 1.3865(18) .
C24 I1 2.0772(12) .
I1 O21 3.0913(10) 4_546
C25 F25 1.3440(15) .
C25 C26 1.3802(18) .
C26 F26 1.3418(14) .
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
O21 H21 N11 0.90(2) 1.75(2) 2.6162(15) 159(2)
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 -0.2(2) .
N11 C12 C13 C14 0.1(2) .
N11 C12 C13 N13 -178.96(13) .
C12 C13 N13 N13 -176.45(15) 5_666
C14 C13 N13 N13 4.5(2) 5_666
C12 C13 C14 C15 0.0(2) .
N13 C13 C14 C15 179.01(13) .
C13 C14 C15 C16 0.0(2) .
C12 N11 C16 C15 0.2(2) .
C14 C15 C16 N11 -0.1(2) .
O21 C21 C22 F22 -1.9(2) .
C26 C21 C22 F22 179.14(13) .
O21 C21 C22 C23 178.04(13) .
C26 C21 C22 C23 -0.9(2) .
F22 C22 C23 F23 0.6(2) .
C21 C22 C23 F23 -179.30(13) .
F22 C22 C23 C24 179.82(13) .
C21 C22 C23 C24 -0.1(2) .
F23 C23 C24 C25 -179.96(13) .
C22 C23 C24 C25 0.8(2) .
F23 C23 C24 I1 2.05(19) .
C22 C23 C24 I1 -177.14(11) .
C25 C24 I1 O21 -21.80(19) 4_546
C23 C24 I1 O21 156.12(10) 4_546
C23 C24 C25 F25 -179.87(12) .
I1 C24 C25 F25 -1.84(17) .
C23 C24 C25 C26 -0.5(2) .
I1 C24 C25 C26 177.48(10) .
F25 C25 C26 F26 -1.82(19) .
C24 C25 C26 F26 178.84(12) .
F25 C25 C26 C21 178.82(12) .
C24 C25 C26 C21 -0.5(2) .
O21 C21 C26 F26 2.83(19) .
C22 C21 C26 F26 -178.12(12) .
O21 C21 C26 C25 -177.80(12) .
C22 C21 C26 C25 1.2(2) .
