#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:26:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180475 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/44/7214414.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_7214414
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Forbes, Safiyyah'
'Desper, John'
_publ_section_title
;
 Altering physical properties of pharmaceutical co-crystals in a
 systematic manner
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              5870
_journal_paper_doi               10.1039/c4ce00206g
_journal_volume                  16
_journal_year                    2014
_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 300 (3-pyridyl)-COHN-(CH2)6-NHCO-(3-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                98.124(3)
_cell_angle_beta                 97.604(3)
_cell_angle_gamma                94.605(3)
_cell_formula_units_Z            1
_cell_length_a                   5.0282(6)
_cell_length_b                   6.7877(8)
_cell_length_c                   17.522(2)
_cell_measurement_reflns_used    2885
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.37
_cell_volume                     583.82(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 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8477
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0487
_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)+(0.0750P)²+0.0300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                2567
_reflns_number_total             3487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00206g2.cif
_cod_data_source_block           sf1005m_8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7214407--7214417.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7214414
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 0.6865(2) 0.54088(17) 0.31012(6) 0.0220(2) Uani 1 1 d .
C12 C 0.5662(2) 0.37938(19) 0.26106(7) 0.0195(3) Uani 1 1 d .
H12 H 0.6483 0.2579 0.2600 0.023 Uiso 1 1 calc R
C13 C 0.3261(2) 0.38179(19) 0.21162(7) 0.0179(3) Uani 1 1 d .
C14 C 0.2016(3) 0.55806(19) 0.21603(7) 0.0204(3) Uani 1 1 d .
H14 H 0.0326 0.5629 0.1853 0.024 Uiso 1 1 calc R
C15 C 0.3269(3) 0.7264(2) 0.26576(8) 0.0227(3) Uani 1 1 d .
H15 H 0.2474 0.8491 0.2689 0.027 Uiso 1 1 calc R
C16 C 0.5706(3) 0.7119(2) 0.31074(8) 0.0229(3) Uani 1 1 d .
H16 H 0.6595 0.8285 0.3435 0.027 Uiso 1 1 calc R
C17 C 0.1985(2) 0.20049(18) 0.15641(7) 0.0175(2) Uani 1 1 d .
N17 N 0.3667(2) 0.07432(16) 0.12859(6) 0.0193(2) Uani 1 1 d .
H17 H 0.532(4) 0.109(2) 0.1354(9) 0.023 Uiso 1 1 d .
O17 O -0.04858(18) 0.17102(14) 0.13749(5) 0.0238(2) Uani 1 1 d .
C21 C 0.2656(2) -0.11096(18) 0.07675(7) 0.0191(3) Uani 1 1 d .
H21A H 0.1805 -0.0796 0.0262 0.023 Uiso 1 1 calc R
H21B H 0.1263 -0.1847 0.0998 0.023 Uiso 1 1 calc R
C22 C 0.4912(2) -0.24162(19) 0.06325(7) 0.0189(3) Uani 1 1 d .
H22A H 0.5757 -0.2733 0.1138 0.023 Uiso 1 1 calc R
H22B H 0.6310 -0.1674 0.0405 0.023 Uiso 1 1 calc R
C23 C 0.3873(2) -0.43498(19) 0.00882(7) 0.0195(3) Uani 1 1 d .
H23A H 0.2945 -0.4026 -0.0406 0.023 Uiso 1 1 calc R
H23B H 0.2535 -0.5116 0.0328 0.023 Uiso 1 1 calc R
C31 C 1.1450(3) 0.2735(2) 0.40265(8) 0.0227(3) Uani 1 1 d .
O31 O 1.1251(2) 0.46795(14) 0.40607(6) 0.0272(2) Uani 1 1 d .
O32 O 0.9880(2) 0.14667(15) 0.36039(6) 0.0325(3) Uani 1 1 d .
C32 C 1.3880(3) 0.2288(2) 0.45503(9) 0.0312(3) Uani 1 1 d .
H32A H 1.4179 0.3296 0.5028 0.037 Uiso 1 1 calc R
H32B H 1.5480 0.2438 0.4282 0.037 Uiso 1 1 calc R
C33 C 1.3674(2) 0.0227(2) 0.47846(8) 0.0212(3) Uani 1 1 d .
H33A H 1.3138 -0.0786 0.4312 0.025 Uiso 1 1 calc R
H33B H 1.2255 0.0133 0.5123 0.025 Uiso 1 1 calc R
H31 H 0.959(3) 0.491(2) 0.3702(9) 0.025 Uiso 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'
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 118.14(11) . .
N11 C12 C13 122.88(12) . .
N11 C12 H12 118.6 . .
C13 C12 H12 118.6 . .
C14 C13 C12 118.08(11) . .
C14 C13 C17 120.06(11) . .
C12 C13 C17 121.84(11) . .
C15 C14 C13 119.29(12) . .
C15 C14 H14 120.4 . .
C13 C14 H14 120.4 . .
C16 C15 C14 118.53(12) . .
C16 C15 H15 120.7 . .
C14 C15 H15 120.7 . .
N11 C16 C15 122.95(12) . .
N11 C16 H16 118.5 . .
C15 C16 H16 118.5 . .
O17 C17 N17 122.40(11) . .
O17 C17 C13 121.29(11) . .
N17 C17 C13 116.30(10) . .
C17 N17 C21 121.32(10) . .
C17 N17 H17 120.0(11) . .
C21 N17 H17 118.1(11) . .
N17 C21 C22 111.16(10) . .
N17 C21 H21A 109.4 . .
C22 C21 H21A 109.4 . .
N17 C21 H21B 109.4 . .
C22 C21 H21B 109.4 . .
H21A C21 H21B 108.0 . .
C21 C22 C23 111.43(10) . .
C21 C22 H22A 109.3 . .
C23 C22 H22A 109.3 . .
C21 C22 H22B 109.3 . .
C23 C22 H22B 109.3 . .
H22A C22 H22B 108.0 . .
C22 C23 C23 112.49(13) . 2_645
C22 C23 H23A 109.1 . .
C23 C23 H23A 109.1 2_645 .
C22 C23 H23B 109.1 . .
C23 C23 H23B 109.1 2_645 .
H23A C23 H23B 107.8 . .
O32 C31 O31 123.34(12) . .
O32 C31 C32 124.09(13) . .
O31 C31 C32 112.54(11) . .
C31 O31 H31 109.8(9) . .
C31 C32 C33 114.77(11) . .
C31 C32 H32A 108.6 . .
C33 C32 H32A 108.6 . .
C31 C32 H32B 108.6 . .
C33 C32 H32B 108.6 . .
H32A C32 H32B 107.6 . .
C32 C33 C33 111.85(13) . 2_856
C32 C33 H33A 109.2 . .
C33 C33 H33A 109.2 2_856 .
C32 C33 H33B 109.2 . .
C33 C33 H33B 109.2 2_856 .
H33A C33 H33B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.3395(17) .
N11 C12 1.3403(16) .
C12 C13 1.3921(17) .
C12 H12 0.9500 .
C13 C14 1.3914(18) .
C13 C17 1.4949(17) .
C14 C15 1.3855(19) .
C14 H14 0.9500 .
C15 C16 1.3849(19) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.2351(15) .
C17 N17 1.3393(16) .
N17 C21 1.4551(16) .
N17 H17 0.835(17) .
C21 C22 1.5174(17) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.5196(17) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C23 1.529(2) 2_645
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C31 O32 1.2118(16) .
C31 O31 1.3254(16) .
C31 C32 1.5061(19) .
O31 H31 1.010(17) .
C32 C33 1.5124(19) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C33 1.519(2) 2_856
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 1.010(17) 1.704(17) 2.7137(15) 177.2(15) .
N17 H17 O17 0.835(17) 2.110(18) 2.9394(14) 172.1(15) 1_655
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 -0.58(19) .
N11 C12 C13 C14 -2.68(19) .
N11 C12 C13 C17 178.89(11) .
C12 C13 C14 C15 3.52(18) .
C17 C13 C14 C15 -178.02(11) .
C13 C14 C15 C16 -1.27(19) .
C12 N11 C16 C15 3.05(19) .
C14 C15 C16 N11 -2.1(2) .
C14 C13 C17 O17 -28.92(18) .
C12 C13 C17 O17 149.48(12) .
C14 C13 C17 N17 150.59(12) .
C12 C13 C17 N17 -31.01(17) .
O17 C17 N17 C21 -2.85(19) .
C13 C17 N17 C21 177.65(11) .
C17 N17 C21 C22 -171.44(11) .
N17 C21 C22 C23 -179.72(10) .
C21 C22 C23 C23 177.30(13) 2_645
O32 C31 C32 C33 -24.7(2) .
O31 C31 C32 C33 157.14(13) .
C31 C32 C33 C33 172.01(14) 2_856
