#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:39:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180514 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/83/7218325.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_7218325
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Welideniya, Dhanushi'
'Desper, John'
'Moore, Curtis'
_publ_section_title
;
 Halogen-bond driven co-crystallization of potential anti-cancer
 compounds: a structural study
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              10203
_journal_paper_doi               10.1039/C4CE01614A
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety
;
(C18 H22 N4 O2) (C8 F16 I2)
;
_chemical_formula_sum            'C26 H22 F16 I2 N4 O2'
_chemical_formula_weight         980.28
_chemical_name_systematic
;
DW-8-18 (3-pyridyl)-CONH-(CH2)6-NHCO-(3-pyridyl), I-(CF2)8-I
;
_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                86.386(2)
_cell_angle_beta                 87.930(2)
_cell_angle_gamma                87.776(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0528(4)
_cell_length_b                   5.1104(4)
_cell_length_c                   29.870(2)
_cell_measurement_reflns_used    9035
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.34
_cell_measurement_theta_min      3.42
_cell_volume                     768.75(10)
_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 0.983
_diffrn_measured_fraction_theta_max 0.925
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            13832
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         31.43
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_T_max  0.8804
_exptl_absorpt_correction_T_min  0.5425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.241
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.003
_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          0.0710
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                4368
_reflns_number_total             4733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01614a2.cif
_cod_data_source_block           A6D8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7218320--7218332.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218325
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 -0.0316(4) 0.5733(4) 0.22186(7) 0.0233(4) Uani 1 1 d .
C12 C 0.1226(4) 0.6390(4) 0.18592(7) 0.0199(4) Uani 1 1 d .
H12 H 0.2687 0.5245 0.1789 0.024 Uiso 1 1 calc R
C13 C 0.0817(4) 0.8653(4) 0.15826(7) 0.0163(3) Uani 1 1 d .
C14 C -0.1340(4) 1.0316(4) 0.16868(7) 0.0196(4) Uani 1 1 d .
H14 H -0.1685 1.1886 0.1508 0.023 Uiso 1 1 calc R
C15 C -0.2973(4) 0.9645(5) 0.20559(8) 0.0236(4) Uani 1 1 d .
H15 H -0.4467 1.0734 0.2132 0.028 Uiso 1 1 calc R
C16 C -0.2382(4) 0.7356(4) 0.23114(8) 0.0235(4) Uani 1 1 d .
H16 H -0.3499 0.6914 0.2565 0.028 Uiso 1 1 calc R
C17 C 0.2670(4) 0.9421(4) 0.12005(7) 0.0161(3) Uani 1 1 d .
N17 N 0.4030(3) 0.7496(3) 0.09990(6) 0.0178(3) Uani 1 1 d .
H17 H 0.363(5) 0.602(6) 0.1052(10) 0.021 Uiso 1 1 d .
O17 O 0.2940(3) 1.1766(3) 0.10801(5) 0.0218(3) Uani 1 1 d .
C21 C 0.5959(4) 0.8103(4) 0.06371(7) 0.0174(4) Uani 1 1 d .
H21A H 0.7269 0.9300 0.0742 0.021 Uiso 1 1 calc R
H21B H 0.5046 0.9014 0.0381 0.021 Uiso 1 1 calc R
C22 C 0.7388(4) 0.5634(4) 0.04833(7) 0.0181(4) Uani 1 1 d .
H22A H 0.6068 0.4396 0.0396 0.022 Uiso 1 1 calc R
H22B H 0.8381 0.4777 0.0736 0.022 Uiso 1 1 calc R
C23 C 0.9308(4) 0.6230(4) 0.00864(7) 0.0172(4) Uani 1 1 d .
H23A H 0.8322 0.7155 -0.0160 0.021 Uiso 1 1 calc R
H23B H 1.0662 0.7418 0.0179 0.021 Uiso 1 1 calc R
C31 C 0.2840(4) -0.0387(4) 0.35203(7) 0.0194(4) Uani 1 1 d .
I1 I 0.14994(2) 0.21997(2) 0.296602(4) 0.01955(6) Uani 1 1 d .
F31A F 0.1018(3) -0.2205(3) 0.36145(5) 0.0265(3) Uani 1 1 d .
F31B F 0.5118(3) -0.1637(3) 0.33972(5) 0.0286(3) Uani 1 1 d .
C32 C 0.3275(4) 0.1113(4) 0.39448(7) 0.0171(4) Uani 1 1 d .
F32A F 0.0974(2) 0.2380(2) 0.40497(4) 0.0229(3) Uani 1 1 d .
F32B F 0.5119(3) 0.2905(2) 0.38388(5) 0.0246(3) Uani 1 1 d .
C33 C 0.4181(4) -0.0634(4) 0.43622(7) 0.0172(4) Uani 1 1 d .
F33A F 0.2371(3) -0.2461(2) 0.44548(4) 0.0235(3) Uani 1 1 d .
F33B F 0.6514(2) -0.1824(3) 0.42524(4) 0.0246(3) Uani 1 1 d .
C34 C 0.4534(4) 0.0879(4) 0.47931(7) 0.0171(4) Uani 1 1 d .
F34A F 0.2196(3) 0.2058(3) 0.49015(4) 0.0241(3) Uani 1 1 d .
F34B F 0.6324(3) 0.2733(2) 0.46989(4) 0.0242(3) 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 117.37(19) . .
C12 N11 I1 122.98(14) . .
C16 N11 I1 116.02(14) . .
N11 C12 C13 123.81(19) . .
N11 C12 H12 118.1 . .
C13 C12 H12 118.1 . .
C12 C13 C14 117.79(18) . .
C12 C13 C17 122.59(17) . .
C14 C13 C17 119.52(18) . .
C15 C14 C13 119.0(2) . .
C15 C14 H14 120.5 . .
C13 C14 H14 120.5 . .
C16 C15 C14 118.7(2) . .
C16 C15 H15 120.7 . .
C14 C15 H15 120.7 . .
N11 C16 C15 123.3(2) . .
N11 C16 H16 118.3 . .
C15 C16 H16 118.3 . .
O17 C17 N17 121.85(18) . .
O17 C17 C13 120.55(17) . .
N17 C17 C13 117.60(17) . .
C17 N17 C21 120.64(16) . .
C17 N17 H17 119(2) . .
C21 N17 H17 119(2) . .
N17 C21 C22 111.31(16) . .
N17 C21 H21A 109.4 . .
C22 C21 H21A 109.4 . .
N17 C21 H21B 109.4 . .
C22 C21 H21B 109.4 . .
H21A C21 H21B 108.0 . .
C21 C22 C23 111.79(16) . .
C21 C22 H22A 109.3 . .
C23 C22 H22A 109.3 . .
C21 C22 H22B 109.3 . .
C23 C22 H22B 109.3 . .
H22A C22 H22B 107.9 . .
C23 C23 C22 112.9(2) 2_765 .
C23 C23 H23A 109.0 2_765 .
C22 C23 H23A 109.0 . .
C23 C23 H23B 109.0 2_765 .
C22 C23 H23B 109.0 . .
H23A C23 H23B 107.8 . .
F31A C31 F31B 107.86(16) . .
F31A C31 C32 109.48(17) . .
F31B C31 C32 109.41(16) . .
F31A C31 I1 108.55(13) . .
F31B C31 I1 109.32(14) . .
C32 C31 I1 112.12(13) . .
C31 I1 N11 179.64(6) . .
F32A C32 F32B 108.59(15) . .
F32A C32 C31 107.45(16) . .
F32B C32 C31 107.84(16) . .
F32A C32 C33 108.98(16) . .
F32B C32 C33 108.75(16) . .
C31 C32 C33 115.07(16) . .
F33A C33 F33B 109.12(16) . .
F33A C33 C32 108.09(16) . .
F33B C33 C32 107.78(16) . .
F33A C33 C34 108.52(16) . .
F33B C33 C34 108.42(16) . .
C32 C33 C34 114.80(16) . .
F34A C34 F34B 108.72(15) . .
F34A C34 C34 108.5(2) . 2_656
F34B C34 C34 108.4(2) . 2_656
F34A C34 C33 108.12(16) . .
F34B C34 C33 108.56(16) . .
C34 C34 C33 114.41(19) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.337(3) .
N11 C16 1.340(3) .
N11 I1 2.9322(19) .
C12 C13 1.391(3) .
C12 H12 0.9500 .
C13 C14 1.394(3) .
C13 C17 1.493(3) .
C14 C15 1.387(3) .
C14 H14 0.9500 .
C15 C16 1.384(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.241(2) .
C17 N17 1.340(2) .
N17 C21 1.456(3) .
N17 H17 0.79(3) .
C21 C22 1.517(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.528(3) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C23 1.524(4) 2_765
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C31 F31A 1.343(2) .
C31 F31B 1.345(2) .
C31 C32 1.549(3) .
C31 I1 2.164(2) .
C32 F32A 1.346(2) .
C32 F32B 1.347(2) .
C32 C33 1.559(3) .
C33 F33A 1.341(2) .
C33 F33B 1.345(2) .
C33 C34 1.562(3) .
C34 F34A 1.344(2) .
C34 F34B 1.345(2) .
C34 C34 1.558(4) 2_656
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
_geom_hbond_site_symmetry_A
N17 H17 O17 0.79(3) 2.21(3) 2.994(2) 169(3) 1_545
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 0.6(3) .
I1 N11 C12 C13 -157.04(16) .
N11 C12 C13 C14 -0.4(3) .
N11 C12 C13 C17 176.0(2) .
C12 C13 C14 C15 -0.3(3) .
C17 C13 C14 C15 -176.84(19) .
C13 C14 C15 C16 0.8(3) .
C12 N11 C16 C15 -0.1(3) .
I1 N11 C16 C15 159.07(18) .
C14 C15 C16 N11 -0.5(3) .
C12 C13 C17 O17 -150.4(2) .
C14 C13 C17 O17 26.0(3) .
C12 C13 C17 N17 29.0(3) .
C14 C13 C17 N17 -154.7(2) .
O17 C17 N17 C21 2.1(3) .
C13 C17 N17 C21 -177.26(18) .
C17 N17 C21 C22 175.97(19) .
N17 C21 C22 C23 176.83(17) .
C21 C22 C23 C23 -177.8(2) 2_765
F31A C31 I1 N11 120(11) .
F31B C31 I1 N11 -122(11) .
C32 C31 I1 N11 -1(11) .
C12 N11 I1 C31 108(11) .
C16 N11 I1 C31 -50(11) .
F31A C31 C32 F32A -63.4(2) .
F31B C31 C32 F32A 178.56(15) .
I1 C31 C32 F32A 57.09(18) .
F31A C31 C32 F32B 179.68(15) .
F31B C31 C32 F32B 61.7(2) .
I1 C31 C32 F32B -59.79(17) .
F31A C31 C32 C33 58.1(2) .
F31B C31 C32 C33 -59.9(2) .
I1 C31 C32 C33 178.65(12) .
F32A C32 C33 F33A 63.8(2) .
F32B C32 C33 F33A -178.03(15) .
C31 C32 C33 F33A -57.0(2) .
F32A C32 C33 F33B -178.42(15) .
F32B C32 C33 F33B -60.2(2) .
C31 C32 C33 F33B 60.8(2) .
F32A C32 C33 C34 -57.5(2) .
F32B C32 C33 C34 60.7(2) .
C31 C32 C33 C34 -178.24(16) .
F33A C33 C34 F34A -61.47(19) .
F33B C33 C34 F34A -179.87(15) .
C32 C33 C34 F34A 59.6(2) .
F33A C33 C34 F34B -179.25(15) .
F33B C33 C34 F34B 62.34(19) .
C32 C33 C34 F34B -58.2(2) .
F33A C33 C34 C34 59.5(2) 2_656
F33B C33 C34 C34 -58.9(3) 2_656
C32 C33 C34 C34 -179.43(19) 2_656
