#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209540.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_7209540
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 H F4 I O2)2
;
_chemical_formula_sum            'C24 H10 F8 I2 N4 O4'
_chemical_formula_weight         824.16
_chemical_name_common
;3,3'-AzoPy 1-HB-XB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-
PhCOOH)2
;
_chemical_name_systematic
;
3,3'-AzoPy 1-HB-XB (3-pyridyl)-N=N-(3-pyridyl), (4-I-F4-PhCOOH)2
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 100.151(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.9020(3)
_cell_length_b                   21.4561(12)
_cell_length_c                   12.1298(7)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.66
_cell_measurement_theta_min      2.55
_cell_volume                     1255.82(13)
_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 0.981
_diffrn_measured_fraction_theta_max 0.899
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13823
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.56
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    2.606
_exptl_absorpt_correction_T_max  0.8186
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0207
_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)+(0.0200P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0508
_reflns_number_gt                3713
_reflns_number_total             4126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26747k.txt
_cod_data_source_block           3,3'-azpy:COOH-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      P2(1)/c
_cod_database_code               7209540
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N -0.0676(3) 0.01018(7) 0.74150(13) 0.0213(3) Uani 1 1 d . . .
H11 H 0.095(5) 0.0424(11) 0.7007(19) 0.026 Uiso 1 1 d . A 1
C12 C -0.1425(4) 0.02582(8) 0.83839(15) 0.0201(3) Uani 1 1 d . . .
H12 H -0.0653 0.0621 0.8766 0.024 Uiso 1 1 calc R . .
C13 C -0.3301(3) -0.00962(8) 0.88449(15) 0.0193(3) Uani 1 1 d . . .
N13 N -0.3986(3) 0.01357(7) 0.98623(13) 0.0207(3) Uani 1 1 d . . .
C14 C -0.4335(4) -0.06410(9) 0.83147(16) 0.0233(3) Uani 1 1 d . . .
H14 H -0.5590 -0.0896 0.8626 0.028 Uiso 1 1 calc R . .
C15 C -0.3497(4) -0.08047(9) 0.73222(17) 0.0264(4) Uani 1 1 d . . .
H15 H -0.4147 -0.1178 0.6945 0.032 Uiso 1 1 calc R . .
C16 C -0.1699(4) -0.04163(9) 0.68874(16) 0.0252(4) Uani 1 1 d . . .
H16 H -0.1176 -0.0521 0.6193 0.030 Uiso 1 1 calc R . .
I1 I 1.13019(2) 0.297628(5) 0.463087(9) 0.01950(4) Uani 0.9839(5) 1 d PD . 1
C21A C 0.5658(4) 0.16044(8) 0.65628(15) 0.0168(3) Uani 0.9839(5) 1 d PD . 1
C22A C 0.6296(4) 0.22116(9) 0.69268(17) 0.0180(3) Uani 0.9839(5) 1 d PD . 1
C23A C 0.7966(5) 0.25910(9) 0.64181(17) 0.0174(3) Uani 0.9839(5) 1 d PD . 1
C24A C 0.9061(4) 0.23925(9) 0.55036(15) 0.0173(3) Uani 0.9839(5) 1 d PD . 1
C25A C 0.8456(4) 0.17893(9) 0.51396(15) 0.0187(3) Uani 0.9839(5) 1 d PD . 1
C26A C 0.6807(4) 0.14055(8) 0.56519(15) 0.0181(3) Uani 0.9839(5) 1 d PD . 1
C27A C 0.3839(4) 0.11942(10) 0.71323(17) 0.0175(3) Uani 0.9839(5) 1 d PD . 1
O21A O 0.2475(3) 0.07789(7) 0.64712(12) 0.0242(3) Uani 0.9839(5) 1 d PD . 1
O22A O 0.3710(3) 0.12583(6) 0.81155(11) 0.0247(3) Uani 0.9839(5) 1 d PD . 1
F22A F 0.5178(3) 0.24600(5) 0.77546(11) 0.0235(3) Uani 0.9839(5) 1 d PD . 1
F23A F 0.8437(4) 0.31747(6) 0.68031(11) 0.0240(4) Uani 0.9839(5) 1 d PD . 1
F25A F 0.9486(4) 0.15663(6) 0.42678(12) 0.0265(3) Uani 0.9839(5) 1 d PD . 1
F26A F 0.6419(3) 0.08250(5) 0.52545(11) 0.0238(2) Uani 0.9839(5) 1 d PD . 1
I2 I 0.3175(19) 0.0992(4) 0.6929(8) 0.0175(3) Uani 0.0161(5) 1 d PD . 2
C21B C 0.904(14) 0.2491(18) 0.543(5) 0.0173(3) Uani 0.0161(5) 1 d PD . 2
C22B C 0.869(18) 0.188(2) 0.502(5) 0.0187(3) Uani 0.0161(5) 1 d PD . 2
C23B C 0.747(12) 0.1429(16) 0.557(5) 0.0181(3) Uani 0.0161(5) 1 d PD . 2
C24B C 0.612(13) 0.1578(18) 0.645(5) 0.0168(3) Uani 0.0161(5) 1 d PD . 2
C25B C 0.647(19) 0.218(2) 0.687(6) 0.0180(3) Uani 0.0161(5) 1 d PD . 2
C26B C 0.798(19) 0.261(2) 0.640(6) 0.0174(3) Uani 0.0161(5) 1 d PD . 2
C27B C 1.094(11) 0.2937(16) 0.498(5) 0.01950(4) Uani 0.0161(5) 1 d PD . 2
O21B O 1.013(13) 0.3515(16) 0.499(6) 0.01950(4) Uani 0.0161(5) 1 d PD . 2
O22B O 1.269(11) 0.274(2) 0.447(6) 0.01950(4) Uani 0.0161(5) 1 d PD . 2
F22B F 0.99(2) 0.170(3) 0.417(7) 0.0265(3) Uani 0.0161(5) 1 d PD . 2
F23B F 0.699(19) 0.087(2) 0.507(7) 0.0238(2) Uani 0.0161(5) 1 d PD . 2
F25B F 0.56(2) 0.232(2) 0.782(6) 0.0235(3) Uani 0.0161(5) 1 d PD . 2
F26B F 0.87(3) 0.313(4) 0.700(9) 0.0240(4) Uani 0.0161(5) 1 d PD . 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'
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 119.55(16) . .
C12 N11 H11 121.0(11) . .
C16 N11 H11 119.5(11) . .
N11 C12 C13 121.52(17) . .
N11 C12 H12 119.2 . .
C13 C12 H12 119.2 . .
C12 C13 C14 119.36(17) . .
C12 C13 N13 115.63(16) . .
C14 C13 N13 125.01(16) . .
N13 N13 C13 112.92(19) 3_457 .
C15 C14 C13 118.50(17) . .
C15 C14 H14 120.7 . .
C13 C14 H14 120.7 . .
C16 C15 C14 119.05(18) . .
C16 C15 H15 120.5 . .
C14 C15 H15 120.5 . .
N11 C16 C15 121.95(18) . .
N11 C16 H16 119.0 . .
C15 C16 H16 119.0 . .
C24A I1 O22A 170.66(6) . 4_665
C26A C21A C22A 116.00(15) . .
C26A C21A C27A 122.70(17) . .
C22A C21A C27A 121.31(16) . .
F22A C22A C23A 117.15(16) . .
F22A C22A C21A 120.79(15) . .
C23A C22A C21A 121.97(15) . .
F23A C23A C22A 118.42(15) . .
F23A C23A C24A 119.95(15) . .
C22A C23A C24A 121.59(16) . .
C23A C24A C25A 116.93(15) . .
C23A C24A I1 122.61(13) . .
C25A C24A I1 120.34(12) . .
F25A C25A C26A 118.44(16) . .
F25A C25A C24A 119.84(15) . .
C26A C25A C24A 121.73(15) . .
F26A C26A C25A 116.88(15) . .
F26A C26A C21A 121.32(16) . .
C25A C26A C21A 121.78(16) . .
O22A C27A O21A 125.0(2) . .
O22A C27A C21A 121.5(2) . .
O21A C27A C21A 113.53(16) . .
C27A O21A H11 111.5(10) . .
C24B I2 H11 164.6(12) . .
C26B C21B C22B 116.0(7) . .
C26B C21B C27B 122.2(9) . .
C22B C21B C27B 120.6(8) . .
F22B C22B C23B 116.9(9) . .
F22B C22B C21B 120.7(9) . .
C23B C22B C21B 121.8(8) . .
F23B C23B C22B 118.0(10) . .
F23B C23B C24B 118.9(9) . .
C22B C23B C24B 121.0(8) . .
C25B C24B C23B 117.0(6) . .
C25B C24B I2 120.4(8) . .
C23B C24B I2 121.7(8) . .
F25B C25B C26B 118.2(9) . .
F25B C25B C24B 119.9(9) . .
C26B C25B C24B 121.5(7) . .
F26B C26B C25B 116.7(9) . .
F26B C26B C21B 121.2(10) . .
C25B C26B C21B 121.6(6) . .
O22B C27B O21B 125.0(11) . .
O22B C27B C21B 120.4(10) . .
O21B C27B C21B 113.0(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.334(2) .
N11 C16 1.336(2) .
N11 H11 1.22(2) .
C12 C13 1.385(2) .
C12 H12 0.9500 .
C13 C14 1.386(3) .
C13 N13 1.425(2) .
N13 N13 1.247(3) 3_457
C14 C15 1.384(3) .
C14 H14 0.9500 .
C15 C16 1.383(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
I1 C24A 2.0751(17) .
I1 O22A 2.8694(13) 4_665
C21A C26A 1.393(2) .
C21A C22A 1.393(2) .
C21A C27A 1.505(3) .
C22A F22A 1.3368(19) .
C22A C23A 1.375(2) .
C23A F23A 1.342(2) .
C23A C24A 1.382(2) .
C24A C25A 1.383(3) .
C25A F25A 1.3380(19) .
C25A C26A 1.376(2) .
C26A F26A 1.337(2) .
C27A O22A 1.213(2) .
C27A O21A 1.302(3) .
O21A H11 1.32(2) .
I2 C24B 2.075(5) .
I2 H11 1.65(3) .
C21B C26B 1.393(5) .
C21B C22B 1.394(5) .
C21B C27B 1.508(6) .
C22B F22B 1.337(5) .
C22B C23B 1.375(6) .
C23B F23B 1.345(6) .
C23B C24B 1.385(5) .
C24B C25B 1.382(5) .
C25B F25B 1.338(5) .
C25B C26B 1.377(5) .
C26B F26B 1.338(6) .
C27B O22B 1.215(6) .
C27B O21B 1.302(6) .
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
N11 H11 O21A 1.22(2) 1.32(2) 2.536(2) 174(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_1
_geom_torsion_site_symmetry_4
C16 N11 C12 C13 -1.7(3) . .
N11 C12 C13 C14 2.9(3) . .
N11 C12 C13 N13 -177.94(16) . .
C12 C13 N13 N13 168.34(19) . 3_457
C14 C13 N13 N13 -12.5(3) . 3_457
C12 C13 C14 C15 -1.5(3) . .
N13 C13 C14 C15 179.43(17) . .
C13 C14 C15 C16 -1.0(3) . .
C12 N11 C16 C15 -0.9(3) . .
C14 C15 C16 N11 2.2(3) . .
C26A C21A C22A F22A 176.28(19) . .
C27A C21A C22A F22A -3.9(3) . .
C26A C21A C22A C23A -0.1(3) . .
C27A C21A C22A C23A 179.71(19) . .
F22A C22A C23A F23A 2.1(3) . .
C21A C22A C23A F23A 178.6(2) . .
F22A C22A C23A C24A -175.4(2) . .
C21A C22A C23A C24A 1.2(3) . .
F23A C23A C24A C25A -178.95(19) . .
C22A C23A C24A C25A -1.5(3) . .
F23A C23A C24A I1 -2.9(3) . .
C22A C23A C24A I1 174.55(16) . .
O22A I1 C24A C23A -119.8(3) 4_665 .
O22A I1 C24A C25A 56.2(4) 4_665 .
C23A C24A C25A F25A -179.08(19) . .
I1 C24A C25A F25A 4.8(3) . .
C23A C24A C25A C26A 0.9(3) . .
I1 C24A C25A C26A -175.25(15) . .
F25A C25A C26A F26A 1.9(3) . .
C24A C25A C26A F26A -178.08(17) . .
F25A C25A C26A C21A -179.94(18) . .
C24A C25A C26A C21A 0.1(3) . .
C22A C21A C26A F26A 177.61(17) . .
C27A C21A C26A F26A -2.2(3) . .
C22A C21A C26A C25A -0.5(3) . .
C27A C21A C26A C25A 179.69(18) . .
C26A C21A C27A O22A 151.55(19) . .
C22A C21A C27A O22A -28.3(3) . .
C26A C21A C27A O21A -28.4(2) . .
C22A C21A C27A O21A 151.73(18) . .
C26B C21B C22B F22B -173(9) . .
C27B C21B C22B F22B -5(9) . .
C26B C21B C22B C23B -2(8) . .
C27B C21B C22B C23B 166(6) . .
F22B C22B C23B F23B -15(9) . .
C21B C22B C23B F23B 174(7) . .
F22B C22B C23B C24B -178(8) . .
C21B C22B C23B C24B 11(8) . .
F23B C23B C24B C25B -174(6) . .
C22B C23B C24B C25B -11(6) . .
F23B C23B C24B I2 -4(7) . .
C22B C23B C24B I2 159(6) . .
C23B C24B C25B F25B -170(9) . .
I2 C24B C25B F25B 21(9) . .
C23B C24B C25B C26B 3(8) . .
I2 C24B C25B C26B -167(7) . .
F25B C25B C26B F26B 6(12) . .
C24B C25B C26B F26B -167(10) . .
F25B C25B C26B C21B 178(10) . .
C24B C25B C26B C21B 5(10) . .
C22B C21B C26B F26B 166(10) . .
C27B C21B C26B F26B -2(10) . .
C22B C21B C26B C25B -6(8) . .
C27B C21B C26B C25B -173(7) . .
C26B C21B C27B O22B 149(7) . .
C22B C21B C27B O22B -18(8) . .
C26B C21B C27B O21B -44(7) . .
C22B C21B C27B O21B 149(6) . .
