#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:39:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180514 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/83/7218331.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_7218331
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
;
(C14 H14 N4 O2) (C6 F12 I2)
;
_chemical_formula_sum            'C20 H14 F12 I2 N4 O2'
_chemical_formula_weight         824.15
_chemical_name_systematic
;
DW-3-9 (3-pyridyl)-CONH-(CH2)2-NHCO-(3-pyridyl), I-(CF2)6-I
;
_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                 103.888(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.7352(8)
_cell_length_b                   9.3958(5)
_cell_length_c                   9.8519(6)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      34.33
_cell_measurement_theta_min      2.65
_cell_volume                     1234.25(12)
_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 0.989
_diffrn_measured_fraction_theta_max 0.956
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20293
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         34.39
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_T_max  0.7402
_exptl_absorpt_correction_T_min  0.4641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0211
_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+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0484
_reflns_number_gt                4517
_reflns_number_total             4958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01614a2.cif
_cod_data_source_block           A2D6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/c
_cod_database_code               7218331
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
N11 N 0.22871(10) 0.47113(13) 0.19249(14) 0.0207(2) Uani 1 1 d .
C12 C 0.17257(10) 0.58535(14) 0.14533(14) 0.0166(2) Uani 1 1 d .
H12 H 0.1711 0.6611 0.2087 0.020 Uiso 1 1 calc R
C13 C 0.11619(9) 0.59886(14) 0.00829(13) 0.0131(2) Uani 1 1 d .
C14 C 0.11895(11) 0.48796(14) -0.08397(15) 0.0163(2) Uani 1 1 d .
H14 H 0.0817 0.4934 -0.1785 0.020 Uiso 1 1 calc R
C15 C 0.17671(11) 0.36965(15) -0.03613(16) 0.0193(3) Uani 1 1 d .
H15 H 0.1795 0.2922 -0.0970 0.023 Uiso 1 1 calc R
C16 C 0.23043(11) 0.36585(15) 0.10198(16) 0.0212(3) Uani 1 1 d .
H16 H 0.2704 0.2845 0.1339 0.025 Uiso 1 1 calc R
C17 C 0.05499(9) 0.72806(13) -0.04281(13) 0.0129(2) Uani 1 1 d .
N17 N 0.03089(8) 0.81155(12) 0.05374(12) 0.01317(19) Uani 1 1 d .
H17 H 0.0415(13) 0.785(2) 0.1343(19) 0.016 Uiso 1 1 d .
O17 O 0.02814(8) 0.75549(11) -0.16906(10) 0.0193(2) Uani 1 1 d .
C21 C -0.03107(10) 0.93669(14) 0.01424(14) 0.0142(2) Uani 1 1 d .
H21A H -0.0639 0.9614 0.0903 0.017 Uiso 1 1 calc R
H21B H -0.0843 0.9156 -0.0707 0.017 Uiso 1 1 calc R
C31 C 0.35070(11) 0.58641(16) 0.69834(15) 0.0191(3) Uani 1 1 d .
I1 I 0.318053(6) 0.521723(10) 0.483167(9) 0.01679(3) Uani 1 1 d .
F31A F 0.26630(7) 0.57239(16) 0.74422(11) 0.0368(3) Uani 1 1 d .
F31B F 0.37593(9) 0.72378(10) 0.71080(10) 0.0325(2) Uani 1 1 d .
C32 C 0.43439(11) 0.49847(15) 0.79439(16) 0.0168(2) Uani 1 1 d .
F32A F 0.40235(9) 0.36419(10) 0.79288(10) 0.0353(3) Uani 1 1 d .
F32B F 0.51506(8) 0.50239(14) 0.74165(12) 0.0343(3) Uani 1 1 d .
C33 C 0.46646(10) 0.55215(15) 0.94805(15) 0.0163(2) Uani 1 1 d .
F33A F 0.38457(7) 0.57949(12) 0.99461(10) 0.0266(2) Uani 1 1 d .
F33B F 0.51699(8) 0.67418(10) 0.94724(10) 0.0296(2) 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
C16 N11 C12 117.60(13) . .
C16 N11 I1 135.77(10) . .
C12 N11 I1 106.63(9) . .
N11 C12 C13 123.38(13) . .
N11 C12 H12 118.3 . .
C13 C12 H12 118.3 . .
C14 C13 C12 118.04(12) . .
C14 C13 C17 119.39(12) . .
C12 C13 C17 122.57(12) . .
C15 C14 C13 118.95(13) . .
C15 C14 H14 120.5 . .
C13 C14 H14 120.5 . .
C14 C15 C16 118.90(13) . .
C14 C15 H15 120.5 . .
C16 C15 H15 120.5 . .
N11 C16 C15 123.13(13) . .
N11 C16 H16 118.4 . .
C15 C16 H16 118.4 . .
O17 C17 N17 121.95(12) . .
O17 C17 C13 121.08(12) . .
N17 C17 C13 116.96(11) . .
C17 N17 C21 121.06(11) . .
C17 N17 H17 120.0(13) . .
C21 N17 H17 118.0(13) . .
N17 C21 C21 111.28(13) . 3_575
N17 C21 H21A 109.4 . .
C21 C21 H21A 109.4 3_575 .
N17 C21 H21B 109.4 . .
C21 C21 H21B 109.4 3_575 .
H21A C21 H21B 108.0 . .
F31B C31 F31A 106.79(13) . .
F31B C31 C32 108.84(12) . .
F31A C31 C32 108.44(12) . .
F31B C31 I1 110.66(10) . .
F31A C31 I1 108.11(10) . .
C32 C31 I1 113.74(10) . .
C31 I1 N11 165.86(5) . .
F32B C32 F32A 108.93(13) . .
F32B C32 C31 108.24(12) . .
F32A C32 C31 107.72(12) . .
F32B C32 C33 107.63(12) . .
F32A C32 C33 109.44(12) . .
C31 C32 C33 114.76(12) . .
F33A C33 F33B 108.47(12) . .
F33A C33 C33 108.08(15) . 3_667
F33B C33 C33 108.53(14) . 3_667
F33A C33 C32 109.33(11) . .
F33B C33 C32 107.30(12) . .
C33 C33 C32 114.96(15) 3_667 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.336(2) .
N11 C12 1.3380(18) .
N11 I1 2.8716(13) .
C12 C13 1.3916(18) .
C12 H12 0.9500 .
C13 C14 1.3892(18) .
C13 C17 1.4934(18) .
C14 C15 1.3811(19) .
C14 H14 0.9500 .
C15 C16 1.384(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.2366(16) .
C17 N17 1.3346(17) .
N17 C21 1.4488(17) .
N17 H17 0.811(18) .
C21 C21 1.529(3) 3_575
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C31 F31B 1.3344(18) .
C31 F31A 1.3480(18) .
C31 C32 1.542(2) .
C31 I1 2.1466(15) .
C32 F32B 1.3325(18) .
C32 F32A 1.3351(16) .
C32 C33 1.556(2) .
C33 F33A 1.3376(17) .
C33 F33B 1.3412(16) .
C33 C33 1.551(3) 3_667
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 0.811(18) 2.026(19) 2.8117(15) 163.2(18) 4_576
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 0.4(2) .
I1 N11 C12 C13 -179.09(11) .
N11 C12 C13 C14 -0.3(2) .
N11 C12 C13 C17 -179.21(13) .
C12 C13 C14 C15 0.2(2) .
C17 C13 C14 C15 179.24(13) .
C13 C14 C15 C16 -0.4(2) .
C12 N11 C16 C15 -0.5(2) .
I1 N11 C16 C15 178.76(11) .
C14 C15 C16 N11 0.5(2) .
C14 C13 C17 O17 -18.7(2) .
C12 C13 C17 O17 160.19(14) .
C14 C13 C17 N17 161.19(13) .
C12 C13 C17 N17 -19.87(19) .
O17 C17 N17 C21 2.0(2) .
C13 C17 N17 C21 -177.92(11) .
C17 N17 C21 C21 -82.40(18) 3_575
F31B C31 I1 N11 -77.1(2) .
F31A C31 I1 N11 39.5(3) .
C32 C31 I1 N11 159.97(15) .
C16 N11 I1 C31 -145.9(2) .
C12 N11 I1 C31 33.4(2) .
F31B C31 C32 F32B -69.57(15) .
F31A C31 C32 F32B 174.62(13) .
I1 C31 C32 F32B 54.31(14) .
F31B C31 C32 F32A 172.79(13) .
F31A C31 C32 F32A 56.97(16) .
I1 C31 C32 F32A -63.34(14) .
F31B C31 C32 C33 50.64(17) .
F31A C31 C32 C33 -65.18(16) .
I1 C31 C32 C33 174.51(9) .
F32B C32 C33 F33A 166.53(12) .
F32A C32 C33 F33A -75.23(15) .
C31 C32 C33 F33A 45.98(16) .
F32B C32 C33 F33B 49.09(15) .
F32A C32 C33 F33B 167.33(12) .
C31 C32 C33 F33B -71.46(15) .
F32B C32 C33 C33 -71.73(18) 3_667
F32A C32 C33 C33 46.5(2) 3_667
C31 C32 C33 C33 167.72(15) 3_667
