#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:03:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178800 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105416.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_4105416
loop_
_publ_author_name
'Christer B. Aakeröy'
'Safiyyah Forbes'
'John Desper'
_publ_section_title
;
 Using Cocrystals To Systematically Modulate Aqueous Solubility and
 Melting Behavior of an Anticancer Drug
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17048
_journal_page_last               17049
_journal_paper_doi               10.1021/ja907674c
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety
;
(C18 H22 N4 O2) (C6 H10 O4)
;
_chemical_formula_sum            'C24 H32 N4 O6'
_chemical_formula_weight         472.54
_chemical_name_systematic
;
SF 2 4-pyridyl-CONH-(CH2)6-NHCO-4-pyridyl, HOOC-(CH2)4-COOH
;
_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                95.094(5)
_cell_angle_beta                 95.603(4)
_cell_angle_gamma                91.076(5)
_cell_formula_units_Z            1
_cell_length_a                   5.1412(4)
_cell_length_b                   5.2394(4)
_cell_length_c                   21.3961(17)
_cell_measurement_reflns_used    2193
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.21
_cell_measurement_theta_min      2.88
_cell_volume                     571.10(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9707
_diffrn_reflns_theta_full        31.49
_diffrn_reflns_theta_max         31.49
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                2666
_reflns_number_total             3695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja907674c_si_002_2.cif
_cod_data_source_block           A2
_cod_database_code               4105416
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 0.6853(2) 0.6222(2) 0.18703(5) 0.0183(2) Uani 1 1 d .
C12 C 0.5269(2) 0.4268(2) 0.19668(6) 0.0180(2) Uani 1 1 d .
H12A H 0.3712 0.3936 0.1691 0.022 Uiso 1 1 calc R
C13 C 0.5808(2) 0.2698(2) 0.24548(6) 0.0177(2) Uani 1 1 d .
H13A H 0.4627 0.1346 0.2514 0.021 Uiso 1 1 calc R
C14 C 0.8105(2) 0.3152(2) 0.28517(5) 0.0153(2) Uani 1 1 d .
C15 C 0.9764(2) 0.5163(2) 0.27463(5) 0.0172(2) Uani 1 1 d .
H15A H 1.1355 0.5513 0.3008 0.021 Uiso 1 1 calc R
C16 C 0.9067(2) 0.6649(2) 0.22555(6) 0.0185(2) Uani 1 1 d .
H16A H 1.0205 0.8027 0.2189 0.022 Uiso 1 1 calc R
C17 C 0.8947(2) 0.1514(2) 0.33746(5) 0.0159(2) Uani 1 1 d .
N17 N 0.7064(2) 0.0334(2) 0.36420(5) 0.0175(2) Uani 1 1 d .
H17 H 0.537(3) 0.068(3) 0.3539(7) 0.021 Uiso 1 1 d .
O17 O 1.12954(16) 0.12901(18) 0.35439(4) 0.0218(2) Uani 1 1 d .
C21 C 0.7754(2) -0.1280(2) 0.41524(6) 0.0178(2) Uani 1 1 d .
H21A H 0.8578 -0.0196 0.4524 0.021 Uiso 1 1 calc R
H21B H 0.9053 -0.2533 0.4018 0.021 Uiso 1 1 calc R
C22 C 0.5399(2) -0.2715(2) 0.43397(5) 0.0174(2) Uani 1 1 d .
H22A H 0.4616 -0.3863 0.3974 0.021 Uiso 1 1 calc R
H22B H 0.4067 -0.1473 0.4460 0.021 Uiso 1 1 calc R
C23 C 0.6164(2) -0.4297(2) 0.48908(6) 0.0175(2) Uani 1 1 d .
H23A H 0.7010 -0.3150 0.5248 0.021 Uiso 1 1 calc R
H23B H 0.7458 -0.5568 0.4764 0.021 Uiso 1 1 calc R
C31 C 0.8259(2) 1.0930(2) 0.09191(6) 0.0172(2) Uani 1 1 d .
O31 O 0.62479(18) 0.92794(18) 0.09132(4) 0.0221(2) Uani 1 1 d .
H31 H 0.647(3) 0.827(3) 0.1249(7) 0.027 Uiso 1 1 d .
O32 O 1.01272(17) 1.10425(18) 0.13137(4) 0.0239(2) Uani 1 1 d .
C32 C 0.7867(2) 1.2634(2) 0.03884(6) 0.0187(3) Uani 1 1 d .
H32A H 0.6414 1.3791 0.0471 0.022 Uiso 1 1 calc R
H32B H 0.7329 1.1547 -0.0007 0.022 Uiso 1 1 calc R
C33 C 1.0248(2) 1.4255(2) 0.02899(5) 0.0183(2) Uani 1 1 d .
H33A H 1.1753 1.3130 0.0238 0.022 Uiso 1 1 calc R
H33B H 1.0700 1.5474 0.0667 0.022 Uiso 1 1 calc R
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'
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 118.13(10) . .
N11 C12 C13 122.78(11) . .
N11 C12 H12A 118.6 . .
C13 C12 H12A 118.6 . .
C14 C13 C12 118.74(11) . .
C14 C13 H13A 120.6 . .
C12 C13 H13A 120.6 . .
C13 C14 C15 118.42(10) . .
C13 C14 C17 123.38(11) . .
C15 C14 C17 118.15(10) . .
C16 C15 C14 119.19(11) . .
C16 C15 H15A 120.4 . .
C14 C15 H15A 120.4 . .
N11 C16 C15 122.73(11) . .
N11 C16 H16A 118.6 . .
C15 C16 H16A 118.6 . .
O17 C17 N17 122.26(11) . .
O17 C17 C14 120.36(10) . .
N17 C17 C14 117.38(10) . .
C17 N17 C21 120.03(10) . .
C17 N17 H17 120.1(10) . .
C21 N17 H17 119.5(10) . .
N17 C21 C22 112.48(10) . .
N17 C21 H21A 109.1 . .
C22 C21 H21A 109.1 . .
N17 C21 H21B 109.1 . .
C22 C21 H21B 109.1 . .
H21A C21 H21B 107.8 . .
C21 C22 C23 111.22(10) . .
C21 C22 H22A 109.4 . .
C23 C22 H22A 109.4 . .
C21 C22 H22B 109.4 . .
C23 C22 H22B 109.4 . .
H22A C22 H22B 108.0 . .
C22 C23 C23 112.98(12) . 2_646
C22 C23 H23A 109.0 . .
C23 C23 H23A 109.0 2_646 .
C22 C23 H23B 109.0 . .
C23 C23 H23B 109.0 2_646 .
H23A C23 H23B 107.8 . .
O32 C31 O31 123.26(11) . .
O32 C31 C32 125.22(11) . .
O31 C31 C32 111.51(10) . .
C31 O31 H31 111.3(10) . .
C31 C32 C33 115.02(10) . .
C31 C32 H32A 108.5 . .
C33 C32 H32A 108.5 . .
C31 C32 H32B 108.5 . .
C33 C32 H32B 108.5 . .
H32A C32 H32B 107.5 . .
C32 C33 C33 111.49(13) . 2_785
C32 C33 H33A 109.3 . .
C33 C33 H33A 109.3 2_785 .
C32 C33 H33B 109.3 . .
C33 C33 H33B 109.3 2_785 .
H33A C33 H33B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.3394(15) .
N11 C16 1.3415(16) .
C12 C13 1.3955(16) .
C12 H12A 0.9500 .
C13 C14 1.3892(17) .
C13 H13A 0.9500 .
C14 C15 1.3908(16) .
C14 C17 1.5053(16) .
C15 C16 1.3853(17) .
C15 H15A 0.9500 .
C16 H16A 0.9500 .
C17 O17 1.2371(14) .
C17 N17 1.3397(15) .
N17 C21 1.4608(15) .
N17 H17 0.902(15) .
C21 C22 1.5185(16) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.5255(16) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C23 1.526(2) 2_646
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C31 O32 1.2122(14) .
C31 O31 1.3339(14) .
C31 C32 1.5063(17) .
O31 H31 0.929(16) .
C32 C33 1.5187(17) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C33 1.527(2) 2_785
C33 H33A 0.9900 .
C33 H33B 0.9900 .
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
O31 H31 N11 0.929(16) 1.780(17) 2.7079(13) 177.6(15) .
N17 H17 O17 0.902(15) 2.127(15) 3.0072(13) 165.0(13) 1_455
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 1.05(17) .
N11 C12 C13 C14 -1.07(18) .
C12 C13 C14 C15 0.27(17) .
C12 C13 C14 C17 -177.19(11) .
C13 C14 C15 C16 0.47(17) .
C17 C14 C15 C16 178.07(11) .
C12 N11 C16 C15 -0.25(17) .
C14 C15 C16 N11 -0.51(18) .
C13 C14 C17 O17 151.11(12) .
C15 C14 C17 O17 -26.35(17) .
C13 C14 C17 N17 -28.89(17) .
C15 C14 C17 N17 153.65(11) .
O17 C17 N17 C21 0.06(19) .
C14 C17 N17 C21 -179.94(10) .
C17 N17 C21 C22 -172.81(11) .
N17 C21 C22 C23 -177.68(10) .
C21 C22 C23 C23 178.06(12) 2_646
O32 C31 C32 C33 11.28(18) .
O31 C31 C32 C33 -169.96(10) .
C31 C32 C33 C33 175.15(13) 2_785
