#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:03:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178800 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105415.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_4105415
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) (C4 H6 O4)
;
_chemical_formula_sum            'C22 H28 N4 O6'
_chemical_formula_weight         444.48
_chemical_name_systematic
;
SF22 4-pyridyl-CONH-(CH2)6)-NHCO-(4-pyridyl), succinic acid CHUNKS
;
_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                118.826(4)
_cell_angle_beta                 91.381(5)
_cell_angle_gamma                99.872(4)
_cell_formula_units_Z            1
_cell_length_a                   5.1754(4)
_cell_length_b                   10.9294(8)
_cell_length_c                   10.9423(8)
_cell_measurement_reflns_used    2329
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.90
_cell_measurement_theta_min      3.70
_cell_volume                     530.11(7)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12293
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0605
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1761
_reflns_number_gt                2108
_reflns_number_total             3228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja907674c_si_002_1.cif
_cod_data_source_block           A1
_cod_database_code               4105415
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 0.5441(3) 0.66307(15) 0.19427(16) 0.0217(3) Uani 1 1 d .
C12 C 0.3763(4) 0.64699(18) 0.27887(19) 0.0218(4) Uani 1 1 d .
H12 H 0.2572 0.7099 0.3140 0.026 Uiso 1 1 calc R
C13 C 0.3668(3) 0.54288(18) 0.31821(19) 0.0204(4) Uani 1 1 d .
H13 H 0.2440 0.5346 0.3783 0.024 Uiso 1 1 calc R
C14 C 0.5419(3) 0.45147(17) 0.26722(17) 0.0176(3) Uani 1 1 d .
C15 C 0.7163(3) 0.46609(18) 0.17783(18) 0.0207(4) Uani 1 1 d .
H15 H 0.8371 0.4044 0.1408 0.025 Uiso 1 1 calc R
C16 C 0.7095(4) 0.57282(18) 0.14417(19) 0.0216(4) Uani 1 1 d .
H16 H 0.8276 0.5824 0.0827 0.026 Uiso 1 1 calc R
C17 C 0.5625(3) 0.33960(17) 0.30763(17) 0.0178(3) Uani 1 1 d .
N17 N 0.3383(3) 0.27618(15) 0.33059(16) 0.0193(3) Uani 1 1 d .
H17 H 0.179(4) 0.296(2) 0.315(2) 0.023 Uiso 1 1 d .
O17 O 0.7788(2) 0.31020(13) 0.31844(14) 0.0242(3) Uani 1 1 d .
C21 C 0.3367(3) 0.15875(18) 0.36021(19) 0.0203(4) Uani 1 1 d .
H21A H 0.5043 0.1778 0.4180 0.024 Uiso 1 1 calc R
H21B H 0.3275 0.0691 0.2705 0.024 Uiso 1 1 calc R
C22 C 0.1070(3) 0.13900(18) 0.43676(19) 0.0204(4) Uani 1 1 d .
H22A H -0.0614 0.1219 0.3805 0.024 Uiso 1 1 calc R
H22B H 0.1185 0.2270 0.5283 0.024 Uiso 1 1 calc R
C23 C 0.1103(3) 0.01283(18) 0.4611(2) 0.0220(4) Uani 1 1 d .
H23A H 0.0982 -0.0745 0.3689 0.026 Uiso 1 1 calc R
H23B H 0.2814 0.0299 0.5151 0.026 Uiso 1 1 calc R
C31 C 0.8143(3) 0.87198(18) 0.05880(19) 0.0207(4) Uani 1 1 d .
O31 O 0.6129(3) 0.87749(14) 0.13219(15) 0.0297(3) Uani 1 1 d .
H31 H 0.585(5) 0.803(3) 0.159(2) 0.036 Uiso 1 1 d .
O32 O 0.9353(3) 0.77700(16) 0.01804(18) 0.0396(4) Uani 1 1 d .
C32 C 0.8709(3) 0.99542(18) 0.03063(19) 0.0216(4) Uani 1 1 d .
H32A H 0.8780 1.0855 0.1196 0.026 Uiso 1 1 calc R
H32B H 0.7243 0.9852 -0.0356 0.026 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 117.80(15) . .
N11 C12 C13 123.43(17) . .
N11 C12 H12 118.3 . .
C13 C12 H12 118.3 . .
C14 C13 C12 118.16(16) . .
C14 C13 H13 120.9 . .
C12 C13 H13 120.9 . .
C13 C14 C15 119.04(15) . .
C13 C14 C17 123.57(15) . .
C15 C14 C17 117.34(15) . .
C16 C15 C14 118.45(16) . .
C16 C15 H15 120.8 . .
C14 C15 H15 120.8 . .
N11 C16 C15 123.10(16) . .
N11 C16 H16 118.5 . .
C15 C16 H16 118.5 . .
O17 C17 N17 123.04(15) . .
O17 C17 C14 120.07(15) . .
N17 C17 C14 116.89(14) . .
C17 N17 C21 120.52(14) . .
C17 N17 H17 120.6(13) . .
C21 N17 H17 118.3(13) . .
N17 C21 C22 112.73(14) . .
N17 C21 H21A 109.0 . .
C22 C21 H21A 109.0 . .
N17 C21 H21B 109.0 . .
C22 C21 H21B 109.0 . .
H21A C21 H21B 107.8 . .
C21 C22 C23 110.53(14) . .
C21 C22 H22A 109.5 . .
C23 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
C23 C22 H22B 109.5 . .
H22A C22 H22B 108.1 . .
C23 C23 C22 113.91(18) 2_556 .
C23 C23 H23A 108.8 2_556 .
C22 C23 H23A 108.8 . .
C23 C23 H23B 108.8 2_556 .
C22 C23 H23B 108.8 . .
H23A C23 H23B 107.7 . .
O32 C31 O31 123.16(16) . .
O32 C31 C32 124.43(16) . .
O31 C31 C32 112.41(15) . .
C31 O31 H31 113.1(14) . .
C31 C32 C32 112.73(18) . 2_775
C31 C32 H32A 109.0 . .
C32 C32 H32A 109.0 2_775 .
C31 C32 H32B 109.0 . .
C32 C32 H32B 109.0 2_775 .
H32A C32 H32B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.336(2) .
N11 C16 1.340(2) .
C12 C13 1.392(2) .
C12 H12 0.9500 .
C13 C14 1.388(2) .
C13 H13 0.9500 .
C14 C15 1.393(2) .
C14 C17 1.505(2) .
C15 C16 1.388(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.234(2) .
C17 N17 1.340(2) .
N17 C21 1.466(2) .
N17 H17 0.92(2) .
C21 C22 1.515(2) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.528(2) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C23 1.508(3) 2_556
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C31 O32 1.208(2) .
C31 O31 1.323(2) .
C31 C32 1.507(2) .
O31 H31 0.98(2) .
C32 C32 1.519(3) 2_775
C32 H32A 0.9900 .
C32 H32B 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 0.98(2) 1.73(2) 2.7094(19) 176(2) .
N17 H17 O17 0.92(2) 2.11(2) 2.9902(19) 161.6(17) 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 0.7(3) .
N11 C12 C13 C14 0.3(3) .
C12 C13 C14 C15 -0.9(2) .
C12 C13 C14 C17 176.61(15) .
C13 C14 C15 C16 0.6(2) .
C17 C14 C15 C16 -177.09(15) .
C12 N11 C16 C15 -1.0(3) .
C14 C15 C16 N11 0.4(3) .
C13 C14 C17 O17 -145.55(18) .
C15 C14 C17 O17 32.0(2) .
C13 C14 C17 N17 34.3(2) .
C15 C14 C17 N17 -148.12(16) .
O17 C17 N17 C21 -4.6(3) .
C14 C17 N17 C21 175.48(14) .
C17 N17 C21 C22 157.76(16) .
N17 C21 C22 C23 178.36(14) .
C21 C22 C23 C23 179.14(18) 2_556
O32 C31 C32 C32 -11.0(3) 2_775
O31 C31 C32 C32 169.94(18) 2_775
