#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:03:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178800 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105419.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_4105419
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) (C12 H22 O4)
;
_chemical_formula_sum            'C30 H44 N4 O6'
_chemical_formula_weight         556.69
_chemical_name_systematic
;
SF5 (4-pyridyl)-CONH-(CH2)6-NHCO-(4-pyridyl), HOOC-(CH2)10-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                86.023(6)
_cell_angle_beta                 89.386(6)
_cell_angle_gamma                88.496(6)
_cell_formula_units_Z            1
_cell_length_a                   5.1519(4)
_cell_length_b                   5.2778(5)
_cell_length_c                   26.148(3)
_cell_measurement_reflns_used    2618
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.18
_cell_measurement_theta_min      2.34
_cell_volume                     709.00(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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0833
_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       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            16574
_diffrn_reflns_theta_full        32.58
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         5028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0650
_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)+(0.0900P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1937
_reflns_number_gt                2850
_reflns_number_total             5028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja907674c_si_002_5.cif
_cod_data_source_block           A5
_cod_original_cell_volume        708.99(11)
_cod_database_code               4105419
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 0.3228(3) 0.3484(3) 0.24705(5) 0.0252(3) Uani 1 1 d .
C12 C 0.5264(3) 0.3099(3) 0.27835(6) 0.0248(3) Uani 1 1 d .
H12 H 0.6430 0.1713 0.2732 0.030 Uiso 1 1 calc R
C13 C 0.5745(3) 0.4635(3) 0.31793(6) 0.0238(3) Uani 1 1 d .
H13 H 0.7223 0.4316 0.3391 0.029 Uiso 1 1 calc R
C14 C 0.4039(3) 0.6645(3) 0.32625(6) 0.0213(3) Uani 1 1 d .
C15 C 0.1921(3) 0.7048(3) 0.29414(6) 0.0241(3) Uani 1 1 d .
H15 H 0.0712 0.8404 0.2989 0.029 Uiso 1 1 calc R
C16 C 0.1592(3) 0.5437(3) 0.25489(6) 0.0249(3) Uani 1 1 d .
H16 H 0.0148 0.5734 0.2328 0.030 Uiso 1 1 calc R
C17 C 0.4643(3) 0.8331(3) 0.36866(6) 0.0220(3) Uani 1 1 d .
N17 N 0.2646(3) 0.9534(3) 0.39019(5) 0.0237(3) Uani 1 1 d .
H17 H 0.113(4) 0.922(3) 0.3823(7) 0.028 Uiso 1 1 d .
O17 O 0.6913(2) 0.8569(2) 0.38219(5) 0.0285(3) Uani 1 1 d .
C21 C 0.3100(3) 1.1188(3) 0.43168(6) 0.0241(3) Uani 1 1 d .
H21A H 0.4469 1.2398 0.4208 0.029 Uiso 1 1 calc R
H21B H 0.3737 1.0141 0.4621 0.029 Uiso 1 1 calc R
C22 C 0.0686(3) 1.2658(3) 0.44635(6) 0.0237(3) Uani 1 1 d .
H22A H -0.0711 1.1457 0.4560 0.028 Uiso 1 1 calc R
H22B H 0.0088 1.3770 0.4165 0.028 Uiso 1 1 calc R
C23 C 0.1201(3) 1.4277(3) 0.49123(6) 0.0238(3) Uani 1 1 d .
H23A H 0.1873 1.3162 0.5204 0.029 Uiso 1 1 calc R
H23B H 0.2561 1.5507 0.4810 0.029 Uiso 1 1 calc R
C31 C 0.5051(3) -0.1291(3) 0.17024(6) 0.0245(3) Uani 1 1 d .
O31 O 0.3073(2) 0.0376(2) 0.16901(5) 0.0295(3) Uani 1 1 d .
H31 H 0.310(3) 0.140(4) 0.1959(8) 0.035 Uiso 1 1 d .
O32 O 0.6718(2) -0.1409(2) 0.20262(5) 0.0305(3) Uani 1 1 d .
C32 C 0.4895(3) -0.3032(3) 0.12699(6) 0.0258(3) Uani 1 1 d .
H32A H 0.4479 -0.1984 0.0951 0.031 Uiso 1 1 calc R
H32B H 0.3433 -0.4187 0.1343 0.031 Uiso 1 1 calc R
C33 C 0.7318(3) -0.4636(3) 0.11724(6) 0.0259(3) Uani 1 1 d .
H33A H 0.7675 -0.5815 0.1476 0.031 Uiso 1 1 calc R
H33B H 0.8825 -0.3521 0.1116 0.031 Uiso 1 1 calc R
C34 C 0.6956(3) -0.6151(3) 0.07033(6) 0.0254(3) Uani 1 1 d .
H34A H 0.5475 -0.7289 0.0770 0.031 Uiso 1 1 calc R
H34B H 0.6494 -0.4952 0.0408 0.031 Uiso 1 1 calc R
C35 C 0.9312(3) -0.7747(3) 0.05551(6) 0.0265(3) Uani 1 1 d .
H35A H 0.9771 -0.8971 0.0846 0.032 Uiso 1 1 calc R
H35B H 1.0804 -0.6623 0.0488 0.032 Uiso 1 1 calc R
C36 C 0.8843(3) -0.9204(3) 0.00817(6) 0.0261(3) Uani 1 1 d .
H36A H 0.7356 -1.0330 0.0152 0.031 Uiso 1 1 calc R
H36B H 0.8355 -0.7973 -0.0206 0.031 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
C12 N11 C16 117.99(13) .
N11 C12 C13 122.88(14) .
N11 C12 H12 118.6 .
C13 C12 H12 118.6 .
C12 C13 C14 119.09(14) .
C12 C13 H13 120.5 .
C14 C13 H13 120.5 .
C15 C14 C13 118.34(14) .
C15 C14 C17 123.55(13) .
C13 C14 C17 118.08(13) .
C14 C15 C16 119.05(14) .
C14 C15 H15 120.5 .
C16 C15 H15 120.5 .
N11 C16 C15 122.64(14) .
N11 C16 H16 118.7 .
C15 C16 H16 118.7 .
O17 C17 N17 122.37(14) .
O17 C17 C14 120.34(13) .
N17 C17 C14 117.29(12) .
C17 N17 C21 119.98(12) .
C17 N17 H17 120.1(13) .
C21 N17 H17 119.6(13) .
N17 C21 C22 112.55(12) .
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 111.14(12) .
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 .
C23 C23 C22 113.18(15) 2_586
C23 C23 H23A 108.9 2_586
C22 C23 H23A 108.9 .
C23 C23 H23B 108.9 2_586
C22 C23 H23B 108.9 .
H23A C23 H23B 107.8 .
O32 C31 O31 123.79(15) .
O32 C31 C32 125.09(14) .
O31 C31 C32 111.11(13) .
C31 O31 H31 112.2(12) .
C31 C32 C33 116.01(12) .
C31 C32 H32A 108.3 .
C33 C32 H32A 108.3 .
C31 C32 H32B 108.3 .
C33 C32 H32B 108.3 .
H32A C32 H32B 107.4 .
C32 C33 C34 110.34(12) .
C32 C33 H33A 109.6 .
C34 C33 H33A 109.6 .
C32 C33 H33B 109.6 .
C34 C33 H33B 109.6 .
H33A C33 H33B 108.1 .
C35 C34 C33 114.96(12) .
C35 C34 H34A 108.5 .
C33 C34 H34A 108.5 .
C35 C34 H34B 108.5 .
C33 C34 H34B 108.5 .
H34A C34 H34B 107.5 .
C34 C35 C36 112.60(12) .
C34 C35 H35A 109.1 .
C36 C35 H35A 109.1 .
C34 C35 H35B 109.1 .
C36 C35 H35B 109.1 .
H35A C35 H35B 107.8 .
C36 C36 C35 114.19(15) 2_735
C36 C36 H36A 108.7 2_735
C35 C36 H36A 108.7 .
C36 C36 H36B 108.7 2_735
C35 C36 H36B 108.7 .
H36A C36 H36B 107.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.340(2) .
N11 C16 1.3402(19) .
C12 C13 1.386(2) .
C12 H12 0.9500 .
C13 C14 1.387(2) .
C13 H13 0.9500 .
C14 C15 1.387(2) .
C14 C17 1.509(2) .
C15 C16 1.392(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.2374(17) .
C17 N17 1.3347(19) .
N17 C21 1.4633(19) .
N17 H17 0.836(18) .
C21 C22 1.509(2) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.528(2) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C23 1.520(3) 2_586
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C31 O32 1.2098(18) .
C31 O31 1.3277(19) .
C31 C32 1.510(2) .
O31 H31 0.92(2) .
C32 C33 1.519(2) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.526(2) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.521(2) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C36 1.526(2) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 C36 1.516(3) 2_735
C36 H36A 0.9900 .
C36 H36B 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 0.92(2) 1.79(2) 2.7085(18) 177.6(19) .
N17 H17 O17 0.836(18) 2.207(19) 3.0222(17) 165.3(18) 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 -0.3(2) .
N11 C12 C13 C14 0.8(2) .
C12 C13 C14 C15 -0.5(2) .
C12 C13 C14 C17 -178.41(14) .
C13 C14 C15 C16 -0.2(2) .
C17 C14 C15 C16 177.56(14) .
C12 N11 C16 C15 -0.5(2) .
C14 C15 C16 N11 0.7(2) .
C15 C14 C17 O17 -151.13(16) .
C13 C14 C17 O17 26.6(2) .
C15 C14 C17 N17 28.6(2) .
C13 C14 C17 N17 -153.66(15) .
O17 C17 N17 C21 -0.6(2) .
C14 C17 N17 C21 179.72(14) .
C17 N17 C21 C22 172.20(14) .
N17 C21 C22 C23 177.60(13) .
C21 C22 C23 C23 -177.88(16) 2_586
O32 C31 C32 C33 -14.1(2) .
O31 C31 C32 C33 167.33(14) .
C31 C32 C33 C34 -175.92(13) .
C32 C33 C34 C35 177.50(14) .
C33 C34 C35 C36 -179.60(14) .
C34 C35 C36 C36 179.38(17) 2_735
