#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:26:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180475 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/44/7214408.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_7214408
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
;
(C16 H18 N4 O2) (C8 H14 O4)
;
_chemical_formula_sum            'C24 H32 N4 O6'
_chemical_formula_weight         472.54
_chemical_name_systematic
;
SF313 (4-pyridyl)-CONH-(CH2)4-NHCO-(4-pyridyl) HOOC-(CH2)6-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                94.963(2)
_cell_angle_beta                 95.404(2)
_cell_angle_gamma                91.630(2)
_cell_formula_units_Z            1
_cell_length_a                   5.1221(4)
_cell_length_b                   5.2045(4)
_cell_length_c                   21.5019(14)
_cell_measurement_reflns_used    5225
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.91
_cell_measurement_theta_min      3.82
_cell_volume                     568.12(7)
_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 0.971
_diffrn_measured_fraction_theta_max 0.887
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10539
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         3.93
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0429
_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+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                3070
_reflns_number_total             3669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00206g2.cif
_cod_data_source_block           sf1002m_2
_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               7214408
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 0.61654(17) 0.47599(17) 0.22842(4) 0.01942(18) Uani 1 1 d .
C12 C 0.45740(19) 0.2793(2) 0.23837(4) 0.0192(2) Uani 1 1 d .
H12 H 0.3007 0.2448 0.2112 0.023 Uiso 1 1 calc R
C13 C 0.51186(19) 0.1227(2) 0.28689(4) 0.01850(19) Uani 1 1 d .
H13 H 0.3934 -0.0145 0.2931 0.022 Uiso 1 1 calc R
C14 C 0.74225(18) 0.17043(18) 0.32606(4) 0.01609(18) Uani 1 1 d .
C15 C 0.90911(19) 0.37330(19) 0.31536(4) 0.01826(19) Uani 1 1 d .
H15 H 1.0690 0.4101 0.3412 0.022 Uiso 1 1 calc R
C16 C 0.83832(19) 0.5212(2) 0.26637(4) 0.0192(2) Uani 1 1 d .
H16 H 0.9523 0.6608 0.2594 0.023 Uiso 1 1 calc R
C17 C 0.82656(18) 0.00674(19) 0.37808(4) 0.01610(18) Uani 1 1 d .
N17 N 0.63730(16) -0.11040(17) 0.40520(4) 0.01802(18) Uani 1 1 d .
H17 H 0.473(3) -0.071(3) 0.3960(6) 0.022 Uiso 1 1 d .
O17 O 1.06208(13) -0.01560(15) 0.39433(3) 0.02149(17) Uani 1 1 d .
C21 C 0.70446(18) -0.27374(19) 0.45580(4) 0.01778(19) Uani 1 1 d .
H21A H 0.7840 -0.1652 0.4932 0.021 Uiso 1 1 calc R
H21B H 0.8359 -0.3980 0.4427 0.021 Uiso 1 1 calc R
C22 C 0.46549(18) -0.41990(19) 0.47259(4) 0.01768(19) Uani 1 1 d .
H22A H 0.3908 -0.5349 0.4357 0.021 Uiso 1 1 calc R
H22B H 0.3306 -0.2961 0.4838 0.021 Uiso 1 1 calc R
C31 C 0.75285(19) 0.94703(19) 0.13312(4) 0.01839(19) Uani 1 1 d .
O31 O 0.55537(15) 0.77614(16) 0.13247(3) 0.02364(18) Uani 1 1 d .
H31 H 0.576(3) 0.674(3) 0.1663(7) 0.028 Uiso 1 1 d .
O32 O 0.93878(15) 0.96577(16) 0.17255(3) 0.02466(18) Uani 1 1 d .
C32 C 0.7120(2) 1.1143(2) 0.07969(5) 0.0212(2) Uani 1 1 d .
H32A H 0.5684 1.2317 0.0883 0.025 Uiso 1 1 calc R
H32B H 0.6523 1.0019 0.0412 0.025 Uiso 1 1 calc R
C33 C 0.94777(19) 1.2760(2) 0.06661(5) 0.0198(2) Uani 1 1 d .
H33A H 1.0968 1.1629 0.0601 0.024 Uiso 1 1 calc R
H33B H 1.0003 1.4015 0.1032 0.024 Uiso 1 1 calc R
C34 C 0.88477(19) 1.4201(2) 0.00862(5) 0.0204(2) Uani 1 1 d .
H34A H 0.8250 1.2934 -0.0273 0.025 Uiso 1 1 calc R
H34B H 0.7382 1.5353 0.0160 0.025 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 118.29(8) . .
N11 C12 C13 122.63(9) . .
N11 C12 H12 118.7 . .
C13 C12 H12 118.7 . .
C14 C13 C12 118.80(9) . .
C14 C13 H13 120.6 . .
C12 C13 H13 120.6 . .
C13 C14 C15 118.60(8) . .
C13 C14 C17 123.32(9) . .
C15 C14 C17 118.03(8) . .
C16 C15 C14 118.80(9) . .
C16 C15 H15 120.6 . .
C14 C15 H15 120.6 . .
N11 C16 C15 122.87(9) . .
N11 C16 H16 118.6 . .
C15 C16 H16 118.6 . .
O17 C17 N17 122.50(9) . .
O17 C17 C14 120.32(9) . .
N17 C17 C14 117.18(8) . .
C17 N17 C21 120.24(8) . .
C17 N17 H17 119.1(9) . .
C21 N17 H17 120.1(9) . .
N17 C21 C22 111.48(8) . .
N17 C21 H21A 109.3 . .
C22 C21 H21A 109.3 . .
N17 C21 H21B 109.3 . .
C22 C21 H21B 109.3 . .
H21A C21 H21B 108.0 . .
C21 C22 C22 111.22(9) . 2_646
C21 C22 H22A 109.4 . .
C22 C22 H22A 109.4 2_646 .
C21 C22 H22B 109.4 . .
C22 C22 H22B 109.4 2_646 .
H22A C22 H22B 108.0 . .
O32 C31 O31 123.59(9) . .
O32 C31 C32 125.10(9) . .
O31 C31 C32 111.29(8) . .
C31 O31 H31 112.0(9) . .
C31 C32 C33 116.29(8) . .
C31 C32 H32A 108.2 . .
C33 C32 H32A 108.2 . .
C31 C32 H32B 108.2 . .
C33 C32 H32B 108.2 . .
H32A C32 H32B 107.4 . .
C32 C33 C34 110.73(8) . .
C32 C33 H33A 109.5 . .
C34 C33 H33A 109.5 . .
C32 C33 H33B 109.5 . .
C34 C33 H33B 109.5 . .
H33A C33 H33B 108.1 . .
C34 C34 C33 113.68(10) 2_785 .
C34 C34 H34A 108.8 2_785 .
C33 C34 H34A 108.8 . .
C34 C34 H34B 108.8 2_785 .
C33 C34 H34B 108.8 . .
H34A C34 H34B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.3349(14) .
N11 C16 1.3373(13) .
C12 C13 1.3912(13) .
C12 H12 0.9500 .
C13 C14 1.3869(13) .
C13 H13 0.9500 .
C14 C15 1.3878(14) .
C14 C17 1.5026(12) .
C15 C16 1.3848(13) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.2355(11) .
C17 N17 1.3364(13) .
N17 C21 1.4597(12) .
N17 H17 0.880(14) .
C21 C22 1.5116(14) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C22 1.5225(17) 2_646
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C31 O32 1.2098(12) .
C31 O31 1.3261(13) .
C31 C32 1.5033(13) .
O31 H31 0.938(15) .
C32 C33 1.5142(14) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.5236(13) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C34 1.517(2) 2_785
C34 H34A 0.9900 .
C34 H34B 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 0.938(15) 1.756(16) 2.6942(11) 178.7(14) .
N17 H17 O17 0.880(14) 2.130(14) 2.9920(11) 166.1(12) 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 0.81(14) .
N11 C12 C13 C14 -0.86(14) .
C12 C13 C14 C15 0.18(13) .
C12 C13 C14 C17 -177.22(8) .
C13 C14 C15 C16 0.48(13) .
C17 C14 C15 C16 178.02(8) .
C12 N11 C16 C15 -0.10(14) .
C14 C15 C16 N11 -0.55(14) .
C13 C14 C17 O17 150.48(10) .
C15 C14 C17 O17 -26.92(13) .
C13 C14 C17 N17 -29.58(13) .
C15 C14 C17 N17 153.01(9) .
O17 C17 N17 C21 -0.43(15) .
C14 C17 N17 C21 179.64(8) .
C17 N17 C21 C22 -170.94(8) .
N17 C21 C22 C22 -177.33(9) 2_646
O32 C31 C32 C33 14.04(15) .
O31 C31 C32 C33 -166.98(9) .
C31 C32 C33 C34 175.84(8) .
C32 C33 C34 C34 -178.14(10) 2_785
