#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/25/7202559.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_7202559
loop_
_publ_author_name
'Christer B. Aakeröy'
'Izhar Hussain'
'Safiyyah Forbes'
'John Desper'
_publ_section_title
;
 Exploring the hydrogen-bond preference of N?H moieties in co-crystals
 assembled via O?H(acid)?N(py) intermolecular interactions
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              46
_journal_paper_doi               10.1039/b614984g
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety
;
(C7 H8 N2 O) (C5 H8 O4)
;
_chemical_formula_sum            'C12 H16 N2 O5'
_chemical_formula_weight         268.27
_chemical_name_common            'N-(4-pyridyl)acetamide, glutaric acid'
_chemical_name_systematic
;
N-(4-pyridyl)acetamide, glutaric acid
;
_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                80.462(7)
_cell_angle_beta                 75.807(7)
_cell_angle_gamma                87.896(7)
_cell_formula_units_Z            2
_cell_length_a                   7.1730(8)
_cell_length_b                   7.6117(8)
_cell_length_c                   11.9194(13)
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.70
_cell_volume                     622.19(12)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.873
_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  0.0867
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3381
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0542
_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          0.1396
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                1710
_reflns_number_total             2213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b614984g.txt
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7202559
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.4933(2) 0.5584(2) 0.64876(15) 0.0246(4) Uani 1 1 d . . .
H11 H 0.419(4) 0.482(3) 0.704(2) 0.030 Uiso 1 1 d . . .
C12 C 0.6838(3) 0.5540(3) 0.63750(19) 0.0275(5) Uani 1 1 d . . .
H12 H 0.7359 0.4726 0.6912 0.033 Uiso 1 1 calc R . .
C13 C 0.8041(3) 0.6646(3) 0.55018(19) 0.0268(5) Uani 1 1 d . . .
H13 H 0.9389 0.6613 0.5435 0.032 Uiso 1 1 calc R . .
C14 C 0.7277(3) 0.7820(2) 0.47129(17) 0.0223(4) Uani 1 1 d . . .
N14 N 0.8340(2) 0.8987(2) 0.37911(16) 0.0241(4) Uani 1 1 d . . .
H14 H 0.772(3) 0.955(3) 0.332(2) 0.029 Uiso 1 1 d . . .
C15 C 0.5277(3) 0.7822(2) 0.48436(18) 0.0236(5) Uani 1 1 d . . .
H15 H 0.4715 0.8599 0.4309 0.028 Uiso 1 1 calc R . .
C16 C 0.4151(3) 0.6702(2) 0.57414(18) 0.0247(5) Uani 1 1 d . . .
H16 H 0.2796 0.6715 0.5840 0.030 Uiso 1 1 calc R . .
C17 C 1.0280(3) 0.9336(3) 0.35399(19) 0.0263(5) Uani 1 1 d . . .
O17 O 1.1326(2) 0.8598(2) 0.41218(15) 0.0402(4) Uani 1 1 d . . .
C18 C 1.0970(3) 1.0728(3) 0.2482(2) 0.0327(5) Uani 1 1 d . . .
H18A H 1.2313 1.1028 0.2417 0.049 Uiso 1 1 calc R . .
H18B H 1.0175 1.1797 0.2560 0.049 Uiso 1 1 calc R . .
H18C H 1.0872 1.0268 0.1778 0.049 Uiso 1 1 calc R . .
C21 C 0.0945(3) 0.3779(3) 0.82751(19) 0.0255(5) Uani 1 1 d . . .
O21 O 0.27151(18) 0.33236(18) 0.82203(13) 0.0294(4) Uani 1 1 d . . .
O22 O 0.0436(2) 0.4848(2) 0.75337(14) 0.0376(4) Uani 1 1 d . . .
C22 C -0.0505(3) 0.2927(3) 0.93779(19) 0.0266(5) Uani 1 1 d . . .
H22A H -0.0226 0.1638 0.9527 0.032 Uiso 1 1 calc R . .
H22B H -0.0321 0.3448 1.0051 0.032 Uiso 1 1 calc R . .
C23 C -0.2587(3) 0.3153(3) 0.93248(18) 0.0249(5) Uani 1 1 d . . .
H23A H -0.2872 0.2356 0.8810 0.030 Uiso 1 1 calc R . .
H23B H -0.2790 0.4395 0.8971 0.030 Uiso 1 1 calc R . .
C24 C -0.3987(3) 0.2737(3) 1.05323(18) 0.0266(5) Uani 1 1 d . . .
H24A H -0.3871 0.3684 1.0989 0.032 Uiso 1 1 calc R . .
H24B H -0.5315 0.2775 1.0425 0.032 Uiso 1 1 calc R . .
C25 C -0.3688(2) 0.0968(3) 1.12332(19) 0.0231(5) Uani 1 1 d . . .
O25 O -0.3288(2) -0.03367(19) 1.06245(13) 0.0300(4) Uani 1 1 d . . .
H25 H -0.309(3) -0.140(3) 1.114(2) 0.036 Uiso 1 1 d . . .
O26 O -0.3834(2) 0.0794(2) 1.22784(15) 0.0380(4) Uani 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
_geom_angle_publ_flag
C16 N11 C12 121.08(18) . . ?
C16 N11 H11 119.5(15) . . ?
C12 N11 H11 119.3(15) . . ?
N11 C12 C13 121.06(19) . . ?
N11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 119.28(17) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N14 C14 C13 124.70(17) . . ?
N14 C14 C15 116.87(18) . . ?
C13 C14 C15 118.42(18) . . ?
C17 N14 C14 127.65(17) . . ?
C17 N14 H14 116.5(15) . . ?
C14 N14 H14 115.8(15) . . ?
C16 C15 C14 119.49(19) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
N11 C16 C15 120.66(17) . . ?
N11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O17 C17 N14 123.07(18) . . ?
O17 C17 C18 123.14(18) . . ?
N14 C17 C18 113.79(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O22 C21 O21 123.78(19) . . ?
O22 C21 C22 120.92(17) . . ?
O21 C21 C22 115.26(17) . . ?
C23 C22 C21 114.77(17) . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 112.82(16) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 114.88(16) . . ?
C25 C24 H24A 108.5 . . ?
C23 C24 H24A 108.5 . . ?
C25 C24 H24B 108.5 . . ?
C23 C24 H24B 108.5 . . ?
H24A C24 H24B 107.5 . . ?
O26 C25 O25 123.90(19) . . ?
O26 C25 C24 121.53(18) . . ?
O25 C25 C24 114.56(19) . . ?
C25 O25 H25 108.8(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.337(3) . ?
N11 C12 1.340(3) . ?
N11 H11 0.88(3) . ?
C12 C13 1.364(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 N14 1.376(3) . ?
C14 C15 1.404(2) . ?
N14 C17 1.376(2) . ?
N14 H14 0.86(2) . ?
C15 C16 1.359(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.206(2) . ?
C17 C18 1.499(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 O22 1.214(2) . ?
C21 O21 1.293(2) . ?
C21 C22 1.525(3) . ?
C22 C23 1.513(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.531(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.500(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O26 1.210(3) . ?
C25 O25 1.308(3) . ?
O25 H25 0.96(3) . ?
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
N11 H11 O21 0.88(3) 1.79(3) 2.677(2) 177(2) .
O25 H25 O21 0.96(3) 1.58(3) 2.5309(19) 170(2) 2_557
N14 H14 O26 0.86(2) 1.97(2) 2.824(2) 177(2) 1_664
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 0.6(3) . . . . ?
N11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 N14 -179.37(19) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 N14 C17 -6.6(3) . . . . ?
C15 C14 N14 C17 174.17(18) . . . . ?
N14 C14 C15 C16 -179.73(17) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C12 N11 C16 C15 0.3(3) . . . . ?
C14 C15 C16 N11 -1.1(3) . . . . ?
C14 N14 C17 O17 1.2(3) . . . . ?
C14 N14 C17 C18 -178.35(18) . . . . ?
O22 C21 C22 C23 14.5(3) . . . . ?
O21 C21 C22 C23 -167.77(16) . . . . ?
C21 C22 C23 C24 -164.60(16) . . . . ?
C22 C23 C24 C25 -51.9(2) . . . . ?
C23 C24 C25 O26 140.06(19) . . . . ?
C23 C24 C25 O25 -40.7(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149265
