#------------------------------------------------------------------------------
#$Date: 2017-07-27 05:05:54 +0300 (Thu, 27 Jul 2017) $
#$Revision: 199358 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/87/7228776.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_7228776
loop_
_publ_author_name
'Krueger, Erika L.'
'Sinha, Abhijeet S.'
'Desper, John'
'Aakeröy, Christer B.'
_publ_section_title
;
 Exploring binding preferences in co-crystals of conformationally flexible
 multitopic ligands
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01177F
_journal_year                    2017
_chemical_formula_moiety
;
(C12 H10 N4 O)2 (C6 H10 O4) (H2 O)2
;
_chemical_formula_sum            'C30 H34 N8 O8'
_chemical_formula_weight         634.65
_chemical_name_systematic
;
EK-D-Adp [(4-pyridyl)-CONH-N=CH-(2-pyridyl)]2, HOOC-(CH2)4-COOH dihydrate
;
_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
_audit_update_record
;
2016-05-09 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                97.862(4)
_cell_angle_beta                 101.861(3)
_cell_angle_gamma                104.541(3)
_cell_formula_units_Z            1
_cell_length_a                   6.5986(6)
_cell_length_b                   8.0173(8)
_cell_length_c                   15.3396(14)
_cell_measurement_reflns_used    8837
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.15
_cell_measurement_theta_min      2.68
_cell_volume                     753.39(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 0.999
_diffrn_measured_fraction_theta_max 0.887
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18394
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         33.17
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0426
_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)+(0.0800P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                4166
_reflns_number_total             5103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce01177f2.cif
_cod_data_source_block           42Adp2H2O
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7228776
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
O1W O 0.93923(11) 0.13694(11) 0.38641(5) 0.02556(17) Uani 1 1 d .
H1A H 0.844(2) 0.1615(19) 0.4142(10) 0.031 Uiso 1 1 d .
H1B H 0.911(2) 0.1660(19) 0.3348(11) 0.031 Uiso 1 1 d .
N11 N 0.38911(13) 0.56620(11) 0.71395(6) 0.01949(17) Uani 1 1 d .
C12 C 0.58841(15) 0.59497(12) 0.70082(6) 0.01835(18) Uani 1 1 d .
H12 H 0.7016 0.6897 0.7401 0.022 Uiso 1 1 calc R
C13 C 0.63551(14) 0.49186(12) 0.63229(6) 0.01665(17) Uani 1 1 d .
H13 H 0.7784 0.5165 0.6244 0.020 Uiso 1 1 calc R
C14 C 0.47234(13) 0.35245(11) 0.57525(6) 0.01468(16) Uani 1 1 d .
C15 C 0.26489(14) 0.32170(13) 0.58893(7) 0.01903(18) Uani 1 1 d .
H15 H 0.1490 0.2270 0.5512 0.023 Uiso 1 1 calc R
C16 C 0.23122(15) 0.43236(13) 0.65882(7) 0.02098(19) Uani 1 1 d .
H16 H 0.0895 0.4120 0.6678 0.025 Uiso 1 1 calc R
C17 C 0.53370(13) 0.24287(11) 0.50348(6) 0.01490(17) Uani 1 1 d .
N17 N 0.36812(12) 0.13247(10) 0.43735(5) 0.01606(16) Uani 1 1 d .
H17 H 0.231(2) 0.1387(17) 0.4298(9) 0.019 Uiso 1 1 d .
O17 O 0.72473(10) 0.25603(9) 0.50720(5) 0.02093(16) Uani 1 1 d .
N21 N 0.10710(13) -0.30734(11) 0.18275(6) 0.02021(17) Uani 1 1 d .
C22 C 0.28822(14) -0.18834(12) 0.23458(6) 0.01650(17) Uani 1 1 d .
C23 C 0.49347(15) -0.17944(12) 0.22141(7) 0.01931(18) Uani 1 1 d .
H23 H 0.6174 -0.0920 0.2592 0.023 Uiso 1 1 calc R
C24 C 0.51338(16) -0.30007(13) 0.15246(7) 0.02219(19) Uani 1 1 d .
H24 H 0.6509 -0.2971 0.1418 0.027 Uiso 1 1 calc R
C25 C 0.32781(17) -0.42537(13) 0.09926(7) 0.0235(2) Uani 1 1 d .
H25 H 0.3357 -0.5108 0.0516 0.028 Uiso 1 1 calc R
C26 C 0.13043(16) -0.42364(13) 0.11690(7) 0.0225(2) Uani 1 1 d .
H26 H 0.0043 -0.5101 0.0801 0.027 Uiso 1 1 calc R
C27 C 0.25489(15) -0.07005(12) 0.30836(6) 0.01818(18) Uani 1 1 d .
H27 H 0.1126 -0.0684 0.3106 0.022 Uiso 1 1 calc R
N27 N 0.41702(12) 0.03078(10) 0.36967(5) 0.01656(16) Uani 1 1 d .
C31 C 0.21609(14) 0.81888(12) 0.86106(7) 0.01801(18) Uani 1 1 d .
O31 O 0.36985(12) 0.74190(11) 0.86603(5) 0.02722(18) Uani 1 1 d .
H31 H 0.361(2) 0.680(2) 0.8059(11) 0.033 Uiso 1 1 d .
O32 O 0.08965(11) 0.81521(11) 0.79030(5) 0.02525(17) Uani 1 1 d .
C32 C 0.21064(14) 0.91459(13) 0.95148(6) 0.01920(18) Uani 1 1 d .
H32A H 0.3272 1.0273 0.9687 0.023 Uiso 1 1 calc R
H32B H 0.2416 0.8435 0.9978 0.023 Uiso 1 1 calc R
C33 C -0.00258(14) 0.95251(13) 0.95327(6) 0.01946(18) Uani 1 1 d .
H33A H -0.1203 0.8405 0.9361 0.023 Uiso 1 1 calc R
H33B H -0.0336 1.0257 0.9081 0.023 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
H1A O1W H1B 106.3(14) . .
C16 N11 C12 118.42(8) . .
N11 C12 C13 122.42(8) . .
N11 C12 H12 118.8 . .
C13 C12 H12 118.8 . .
C12 C13 C14 119.31(8) . .
C12 C13 H13 120.3 . .
C14 C13 H13 120.3 . .
C13 C14 C15 118.43(8) . .
C13 C14 C17 116.99(7) . .
C15 C14 C17 124.57(8) . .
C16 C15 C14 118.55(8) . .
C16 C15 H15 120.7 . .
C14 C15 H15 120.7 . .
N11 C16 C15 122.87(8) . .
N11 C16 H16 118.6 . .
C15 C16 H16 118.6 . .
O17 C17 N17 123.87(8) . .
O17 C17 C14 120.23(8) . .
N17 C17 C14 115.90(7) . .
C17 N17 N27 117.87(7) . .
C17 N17 H17 122.4(8) . .
N27 N17 H17 118.6(8) . .
C26 N21 C22 116.80(8) . .
N21 C22 C23 123.26(8) . .
N21 C22 C27 114.58(8) . .
C23 C22 C27 122.13(8) . .
C24 C23 C22 118.89(9) . .
C24 C23 H23 120.6 . .
C22 C23 H23 120.6 . .
C23 C24 C25 118.41(9) . .
C23 C24 H24 120.8 . .
C25 C24 H24 120.8 . .
C24 C25 C26 118.74(9) . .
C24 C25 H25 120.6 . .
C26 C25 H25 120.6 . .
N21 C26 C25 123.88(9) . .
N21 C26 H26 118.1 . .
C25 C26 H26 118.1 . .
N27 C27 C22 119.96(8) . .
N27 C27 H27 120.0 . .
C22 C27 H27 120.0 . .
C27 N27 N17 115.40(7) . .
O32 C31 O31 123.75(9) . .
O32 C31 C32 122.71(8) . .
O31 C31 C32 113.54(8) . .
C31 O31 H31 109.2(9) . .
C31 C32 C33 114.27(8) . .
C31 C32 H32A 108.7 . .
C33 C32 H32A 108.7 . .
C31 C32 H32B 108.7 . .
C33 C32 H32B 108.7 . .
H32A C32 H32B 107.6 . .
C32 C33 C33 111.43(9) . 2_577
C32 C33 H33A 109.3 . .
C33 C33 H33A 109.3 2_577 .
C32 C33 H33B 109.3 . .
C33 C33 H33B 109.3 2_577 .
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
O1W H1A 0.873(15) .
O1W H1B 0.853(16) .
N11 C16 1.3342(12) .
N11 C12 1.3389(12) .
C12 C13 1.3823(12) .
C12 H12 0.9500 .
C13 C14 1.3838(12) .
C13 H13 0.9500 .
C14 C15 1.3933(12) .
C14 C17 1.4983(12) .
C15 C16 1.3866(13) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.2269(10) .
C17 N17 1.3489(11) .
N17 N27 1.3729(10) .
N17 H17 0.905(13) .
N21 C26 1.3385(12) .
N21 C22 1.3417(11) .
C22 C23 1.3958(13) .
C22 C27 1.4636(12) .
C23 C24 1.3829(13) .
C23 H23 0.9500 .
C24 C25 1.3862(14) .
C24 H24 0.9500 .
C25 C26 1.3867(14) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 N27 1.2754(12) .
C27 H27 0.9500 .
C31 O32 1.2172(12) .
C31 O31 1.3083(11) .
C31 C32 1.5023(13) .
O31 H31 0.970(16) .
C32 C33 1.5170(12) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C33 1.5180(18) 2_577
C33 H33A 0.9900 .
C33 H33B 0.9900 .
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 0.30(15) .
N11 C12 C13 C14 -0.59(15) .
C12 C13 C14 C15 0.33(14) .
C12 C13 C14 C17 -178.71(8) .
C13 C14 C15 C16 0.19(14) .
C17 C14 C15 C16 179.15(8) .
C12 N11 C16 C15 0.26(15) .
C14 C15 C16 N11 -0.51(16) .
C13 C14 C17 O17 13.69(13) .
C15 C14 C17 O17 -165.28(9) .
C13 C14 C17 N17 -166.58(8) .
C15 C14 C17 N17 14.45(13) .
O17 C17 N17 N27 -0.92(14) .
C14 C17 N17 N27 179.37(7) .
C26 N21 C22 C23 1.38(14) .
C26 N21 C22 C27 -177.07(8) .
N21 C22 C23 C24 -0.88(15) .
C27 C22 C23 C24 177.46(9) .
C22 C23 C24 C25 -0.11(15) .
C23 C24 C25 C26 0.50(15) .
C22 N21 C26 C25 -0.96(15) .
C24 C25 C26 N21 0.04(16) .
N21 C22 C27 N27 169.78(9) .
C23 C22 C27 N27 -8.69(15) .
C22 C27 N27 N17 -178.02(8) .
C17 N17 N27 C27 -179.35(8) .
O32 C31 C32 C33 19.59(14) .
O31 C31 C32 C33 -160.89(9) .
C31 C32 C33 C33 179.40(10) 2_577
