#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:39:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180514 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/83/7218329.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_7218329
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
;
(C16 H18 N4 O2) (C8 F16 I2)
;
_chemical_formula_sum            'C24 H18 F16 I2 N4 O2'
_chemical_formula_weight         952.22
_chemical_name_systematic
;
DW-6-18  (3-pyridyl)-COHN-(CH2)4-NHCO-(3-pyridyl), I-(CF2)8-I
;
_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                 92.370(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   54.569(3)
_cell_length_b                   5.6337(3)
_cell_length_c                   9.7038(6)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.59
_cell_measurement_theta_min      2.99
_cell_volume                     2980.6(3)
_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 0.980
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       82
_diffrn_reflns_limit_h_min       -77
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16963
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.56
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_T_max  0.8772
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0266
_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)+(0.0300P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0641
_reflns_number_gt                4249
_reflns_number_total             4886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01614a2.cif
_cod_data_source_block           A4D8
_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      C2/c
_cod_database_code               7218329
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 0.10261(3) -0.7477(3) 0.60843(17) 0.0280(3) Uani 1 1 d .
C12 C 0.08335(3) -0.6258(3) 0.55566(19) 0.0239(3) Uani 1 1 d .
H12 H 0.0790 -0.4821 0.5995 0.029 Uiso 1 1 calc R
C13 C 0.06941(3) -0.6985(3) 0.43997(18) 0.0218(3) Uani 1 1 d .
C14 C 0.07621(4) -0.9070(4) 0.3743(2) 0.0272(4) Uani 1 1 d .
H14 H 0.0674 -0.9605 0.2938 0.033 Uiso 1 1 calc R
C15 C 0.09599(4) -1.0344(4) 0.4285(2) 0.0315(4) Uani 1 1 d .
H15 H 0.1009 -1.1782 0.3865 0.038 Uiso 1 1 calc R
C16 C 0.10861(4) -0.9492(4) 0.5451(2) 0.0302(4) Uani 1 1 d .
H16 H 0.1222 -1.0380 0.5818 0.036 Uiso 1 1 calc R
C17 C 0.04826(3) -0.5573(3) 0.38083(19) 0.0218(3) Uani 1 1 d .
N17 N 0.03733(3) -0.4085(3) 0.46543(16) 0.0232(3) Uani 1 1 d .
H17 H 0.0404(5) -0.417(5) 0.551(3) 0.028 Uiso 1 1 d .
O17 O 0.04139(3) -0.5789(3) 0.25854(14) 0.0299(3) Uani 1 1 d .
C21 C 0.01739(3) -0.2554(3) 0.41508(18) 0.0238(3) Uani 1 1 d .
H21A H 0.0030 -0.3537 0.3863 0.029 Uiso 1 1 calc R
H21B H 0.0226 -0.1658 0.3336 0.029 Uiso 1 1 calc R
C22 C 0.01017(3) -0.0828(4) 0.52638(19) 0.0241(3) Uani 1 1 d .
H22A H 0.0247 0.0121 0.5570 0.029 Uiso 1 1 calc R
H22B H 0.0045 -0.1726 0.6068 0.029 Uiso 1 1 calc R
C31 C 0.16986(3) -0.2342(3) 0.8373(2) 0.0260(4) Uani 1 1 d .
F31A F 0.16212(2) -0.1170(3) 0.94749(15) 0.0395(3) Uani 1 1 d .
F31B F 0.17373(3) -0.0739(3) 0.73865(16) 0.0417(3) Uani 1 1 d .
I1 I 0.141970(2) -0.47715(2) 0.759701(13) 0.02588(5) Uani 1 1 d .
C32 C 0.19408(3) -0.3623(3) 0.87777(19) 0.0232(3) Uani 1 1 d .
F32A F 0.18909(2) -0.5340(2) 0.96783(15) 0.0345(3) Uani 1 1 d .
F32B F 0.20263(2) -0.4620(3) 0.76388(14) 0.0366(3) Uani 1 1 d .
C33 C 0.21449(3) -0.1996(3) 0.94480(18) 0.0227(3) Uani 1 1 d .
F33A F 0.21589(3) 0.0002(2) 0.87055(16) 0.0368(3) Uani 1 1 d .
F33B F 0.20764(2) -0.1425(3) 1.07130(12) 0.0345(3) Uani 1 1 d .
C34 C 0.24031(3) -0.3160(3) 0.95385(19) 0.0243(3) Uani 1 1 d .
F34A F 0.23829(3) -0.5367(2) 1.00108(19) 0.0442(4) Uani 1 1 d .
F34B F 0.24835(2) -0.3239(3) 0.82540(13) 0.0476(4) 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 117.53(18) . .
C16 N11 I1 118.45(13) . .
C12 N11 I1 117.76(13) . .
N11 C12 C13 123.50(18) . .
N11 C12 H12 118.3 . .
C13 C12 H12 118.3 . .
C12 C13 C14 118.02(17) . .
C12 C13 C17 122.70(16) . .
C14 C13 C17 119.23(17) . .
C15 C14 C13 118.84(19) . .
C15 C14 H14 120.6 . .
C13 C14 H14 120.6 . .
C14 C15 C16 118.97(19) . .
C14 C15 H15 120.5 . .
C16 C15 H15 120.5 . .
N11 C16 C15 123.13(19) . .
N11 C16 H16 118.4 . .
C15 C16 H16 118.4 . .
O17 C17 N17 121.90(17) . .
O17 C17 C13 120.96(17) . .
N17 C17 C13 117.14(16) . .
C17 N17 C21 120.88(16) . .
C17 N17 H17 119.9(18) . .
C21 N17 H17 118.6(18) . .
N17 C21 C22 110.67(15) . .
N17 C21 H21A 109.5 . .
C22 C21 H21A 109.5 . .
N17 C21 H21B 109.5 . .
C22 C21 H21B 109.5 . .
H21A C21 H21B 108.1 . .
C21 C22 C22 111.13(19) . 5_556
C21 C22 H22A 109.4 . .
C22 C22 H22A 109.4 5_556 .
C21 C22 H22B 109.4 . .
C22 C22 H22B 109.4 5_556 .
H22A C22 H22B 108.0 . .
F31B C31 F31A 107.59(17) . .
F31B C31 C32 109.83(16) . .
F31A C31 C32 108.80(15) . .
F31B C31 I1 107.94(13) . .
F31A C31 I1 110.45(12) . .
C32 C31 I1 112.12(13) . .
C31 I1 N11 169.13(6) . .
F32A C32 F32B 108.81(16) . .
F32A C32 C31 108.01(15) . .
F32B C32 C31 108.03(15) . .
F32A C32 C33 108.21(15) . .
F32B C32 C33 108.82(15) . .
C31 C32 C33 114.83(15) . .
F33B C33 F33A 108.42(16) . .
F33B C33 C34 109.69(14) . .
F33A C33 C34 108.25(15) . .
F33B C33 C32 107.56(15) . .
F33A C33 C32 108.93(15) . .
C34 C33 C32 113.88(15) . .
F34A C34 F34B 108.92(17) . .
F34A C34 C34 108.3(2) . 7_547
F34B C34 C34 108.19(19) . 7_547
F34A C34 C33 109.04(16) . .
F34B C34 C33 107.03(15) . .
C34 C34 C33 115.24(19) 7_547 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.338(3) .
N11 C12 1.339(2) .
N11 I1 2.9716(17) .
C12 C13 1.391(3) .
C12 H12 0.9500 .
C13 C14 1.393(3) .
C13 C17 1.497(3) .
C14 C15 1.382(3) .
C14 H14 0.9500 .
C15 C16 1.385(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.235(2) .
C17 N17 1.331(2) .
N17 C21 1.457(2) .
N17 H17 0.84(3) .
C21 C22 1.517(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C22 1.523(4) 5_556
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C31 F31B 1.339(2) .
C31 F31A 1.340(2) .
C31 C32 1.542(3) .
C31 I1 2.1592(19) .
C32 F32A 1.339(2) .
C32 F32B 1.341(2) .
C32 C33 1.563(3) .
C33 F33B 1.337(2) .
C33 F33A 1.341(2) .
C33 C34 1.553(3) .
C34 F34A 1.331(2) .
C34 F34B 1.339(2) .
C34 C34 1.548(4) 7_547
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 0.84(3) 2.01(3) 2.845(2) 170(2) 6_546
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(3) .
I1 N11 C12 C13 152.13(15) .
N11 C12 C13 C14 -1.3(3) .
N11 C12 C13 C17 -178.72(17) .
C12 C13 C14 C15 1.5(3) .
C17 C13 C14 C15 179.05(18) .
C13 C14 C15 C16 -0.9(3) .
C12 N11 C16 C15 0.4(3) .
I1 N11 C16 C15 -151.21(17) .
C14 C15 C16 N11 -0.1(3) .
C12 C13 C17 O17 156.12(19) .
C14 C13 C17 O17 -21.3(3) .
C12 C13 C17 N17 -23.8(3) .
C14 C13 C17 N17 158.81(18) .
O17 C17 N17 C21 -3.0(3) .
C13 C17 N17 C21 176.90(16) .
C17 N17 C21 C22 -173.15(17) .
N17 C21 C22 C22 178.4(2) 5_556
F31B C31 I1 N11 -8.1(4) .
F31A C31 I1 N11 109.3(3) .
C32 C31 I1 N11 -129.2(3) .
C16 N11 I1 C31 106.7(3) .
C12 N11 I1 C31 -44.9(4) .
F31B C31 C32 F32A -174.93(16) .
F31A C31 C32 F32A 67.5(2) .
I1 C31 C32 F32A -54.93(17) .
F31B C31 C32 F32B -57.4(2) .
F31A C31 C32 F32B -174.93(15) .
I1 C31 C32 F32B 62.61(17) .
F31B C31 C32 C33 64.2(2) .
F31A C31 C32 C33 -53.3(2) .
I1 C31 C32 C33 -175.76(12) .
F32A C32 C33 F33B -49.19(19) .
F32B C32 C33 F33B -167.28(15) .
C31 C32 C33 F33B 71.5(2) .
F32A C32 C33 F33A -166.50(15) .
F32B C32 C33 F33A 75.41(19) .
C31 C32 C33 F33A -45.8(2) .
F32A C32 C33 C34 72.58(19) .
F32B C32 C33 C34 -45.5(2) .
C31 C32 C33 C34 -166.70(15) .
F33B C33 C34 F34A 74.91(19) .
F33A C33 C34 F34A -166.96(16) .
C32 C33 C34 F34A -45.7(2) .
F33B C33 C34 F34B -167.41(16) .
F33A C33 C34 F34B -49.3(2) .
C32 C33 C34 F34B 72.0(2) .
F33B C33 C34 C34 -47.1(3) 7_547
F33A C33 C34 C34 71.1(2) 7_547
C32 C33 C34 C34 -167.7(2) 7_547
