#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:48:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180356 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/25/7202555.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_7202555
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)2 (C10 H18 O4)
;
_chemical_formula_sum            'C24 H34 N4 O6'
_chemical_formula_weight         474.55
_chemical_name_common            'N-(4-pyridyl)acetamide, sebacic acid'
_chemical_name_systematic
;
N-(4-pyridyl)acetamide, sebacic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.987(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.532(3)
_cell_length_b                   8.2965(8)
_cell_length_c                   10.6120(10)
_cell_measurement_reflns_used    1717
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.65
_cell_measurement_theta_min      2.75
_cell_volume                     2457.3(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14481
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0555
_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+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                3007
_reflns_number_total             3740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b614984g.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        2457.2(4)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7202555
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.27526(4) 0.44681(14) 0.50826(11) 0.0187(2) Uani 1 1 d . . .
C12 C 0.26614(4) 0.39198(16) 0.38623(12) 0.0183(3) Uani 1 1 d . . .
H12 H 0.2364 0.4185 0.3314 0.022 Uiso 1 1 calc R . .
C13 C 0.29829(4) 0.29880(16) 0.33766(12) 0.0177(3) Uani 1 1 d . . .
H13 H 0.2905 0.2616 0.2511 0.021 Uiso 1 1 calc R . .
C14 C 0.34252(4) 0.25933(15) 0.41701(12) 0.0161(2) Uani 1 1 d . . .
C15 C 0.35179(5) 0.31372(17) 0.54485(13) 0.0198(3) Uani 1 1 d . . .
H15 H 0.3810 0.2878 0.6025 0.024 Uiso 1 1 calc R . .
C16 C 0.31716(5) 0.40630(17) 0.58448(13) 0.0205(3) Uani 1 1 d . . .
H16 H 0.3235 0.4434 0.6711 0.025 Uiso 1 1 calc R . .
C17 C 0.42033(4) 0.12258(15) 0.42039(13) 0.0180(3) Uani 1 1 d . . .
N17 N 0.37454(4) 0.17047(14) 0.36232(11) 0.0175(2) Uani 1 1 d . . .
H17 H 0.3656(6) 0.151(2) 0.2828(18) 0.021 Uiso 1 1 d . . .
O17 O 0.43793(4) 0.14497(13) 0.53349(9) 0.0239(2) Uani 1 1 d . . .
C18 C 0.44709(5) 0.04294(18) 0.32863(13) 0.0224(3) Uani 1 1 d . . .
H18A H 0.4724 -0.0260 0.3772 0.034 Uiso 1 1 calc R . .
H18B H 0.4614 0.1258 0.2826 0.034 Uiso 1 1 calc R . .
H18C H 0.4248 -0.0228 0.2666 0.034 Uiso 1 1 calc R . .
C21 C 0.17508(4) 0.65193(16) 0.51364(12) 0.0169(2) Uani 1 1 d . . .
O21 O 0.21454(3) 0.61651(13) 0.59567(9) 0.0227(2) Uani 1 1 d . . .
H21 H 0.2396(7) 0.540(2) 0.5498(17) 0.027 Uiso 1 1 d . . .
O22 O 0.16650(4) 0.60678(12) 0.40136(9) 0.0223(2) Uani 1 1 d . . .
C22 C 0.14173(5) 0.75547(16) 0.57235(13) 0.0201(3) Uani 1 1 d . . .
H22A H 0.1584 0.8578 0.6013 0.024 Uiso 1 1 calc R . .
H22B H 0.1356 0.6998 0.6498 0.024 Uiso 1 1 calc R . .
C23 C 0.09401(5) 0.79547(18) 0.48578(15) 0.0247(3) Uani 1 1 d . . .
H23A H 0.0768 0.6941 0.4568 0.030 Uiso 1 1 calc R . .
H23B H 0.0996 0.8530 0.4085 0.030 Uiso 1 1 calc R . .
C24 C 0.06286(5) 0.89970(18) 0.55361(16) 0.0274(3) Uani 1 1 d . . .
H24A H 0.0550 0.8382 0.6265 0.033 Uiso 1 1 calc R . .
H24B H 0.0813 0.9962 0.5895 0.033 Uiso 1 1 calc R . .
C25 C 0.01647(5) 0.95348(19) 0.46502(17) 0.0300(3) Uani 1 1 d . . .
H25A H -0.0007 0.8573 0.4237 0.045 Uiso 1 1 calc R . .
H25B H 0.0243 1.0224 0.3960 0.045 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
_geom_angle_publ_flag
C16 N11 C12 117.78(11) . . ?
C16 N11 H21 123.8(8) . . ?
C12 N11 H21 118.4(8) . . ?
N11 C12 C13 122.59(12) . . ?
N11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C12 C13 C14 119.46(12) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N17 C14 C15 124.47(11) . . ?
N17 C14 C13 117.40(11) . . ?
C15 C14 C13 118.12(11) . . ?
C16 C15 C14 118.01(12) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
N11 C16 C15 124.03(12) . . ?
N11 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
O17 C17 N17 123.70(12) . . ?
O17 C17 C18 122.93(12) . . ?
N17 C17 C18 113.35(11) . . ?
C17 N17 C14 127.46(11) . . ?
C17 N17 H17 116.9(12) . . ?
C14 N17 H17 115.4(12) . . ?
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 123.39(12) . . ?
O22 C21 C22 124.07(11) . . ?
O21 C21 C22 112.53(11) . . ?
C21 O21 H21 111.8(9) . . ?
C21 C22 C23 116.06(11) . . ?
C21 C22 H22A 108.3 . . ?
C23 C22 H22A 108.3 . . ?
C21 C22 H22B 108.3 . . ?
C23 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 C24 112.16(12) . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 113.09(13) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C25 113.13(17) . 5_576 ?
C24 C25 H25A 109.0 . . ?
C25 C25 H25A 109.0 5_576 . ?
C24 C25 H25B 109.0 . . ?
C25 C25 H25B 109.0 5_576 . ?
H25A C25 H25B 107.8 . . ?
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 1.3398(17) . ?
N11 C12 1.3460(17) . ?
N11 H21 1.421(19) . ?
C12 C13 1.3788(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.4027(17) . ?
C13 H13 0.9500 . ?
C14 N17 1.3911(16) . ?
C14 C15 1.4018(17) . ?
C15 C16 1.3841(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2152(16) . ?
C17 N17 1.3821(16) . ?
C17 C18 1.5089(18) . ?
N17 H17 0.845(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 O22 1.2243(16) . ?
C21 O21 1.3056(15) . ?
C21 C22 1.5092(17) . ?
O21 H21 1.136(19) . ?
C22 C23 1.5129(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.524(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.523(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C25 1.523(3) 5_576 ?
C25 H25A 0.9900 . ?
C25 H25B 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
O21 H21 N11 1.136(19) 1.421(19) 2.5516(15) 172.5(17) .
N17 H17 O22 0.845(19) 2.012(19) 2.8494(15) 170.8(17) 4_545
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 -0.84(19) . . . . ?
N11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 N17 -177.52(12) . . . . ?
C12 C13 C14 C15 1.53(19) . . . . ?
N17 C14 C15 C16 177.57(12) . . . . ?
C13 C14 C15 C16 -1.41(19) . . . . ?
C12 N11 C16 C15 1.0(2) . . . . ?
C14 C15 C16 N11 0.2(2) . . . . ?
O17 C17 N17 C14 4.8(2) . . . . ?
C18 C17 N17 C14 -173.77(12) . . . . ?
C15 C14 N17 C17 -1.2(2) . . . . ?
C13 C14 N17 C17 177.83(12) . . . . ?
O22 C21 C22 C23 3.47(19) . . . . ?
O21 C21 C22 C23 -177.09(12) . . . . ?
C21 C22 C23 C24 179.81(12) . . . . ?
C22 C23 C24 C25 175.05(13) . . . . ?
C23 C24 C25 C25 175.47(16) . . . 5_576 ?
