#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:29:14 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179581 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/46/4504645.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_4504645
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Hussain, Izhar'
'Desper, John'
_publ_section_title
;
 2-Acetaminopyridine:  A Highly Effective Cocrystallizing Agent
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              474
_journal_paper_doi               10.1021/cg050391z
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety
;
(C7 H8 N2 O)2 (C9 H16 O4)
;
_chemical_formula_sum            'C23 H32 N4 O6'
_chemical_formula_weight         460.53
_chemical_name_systematic
;
[N-(2-pyridyl)acetamide]2, nonanedioic 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                 114.909(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.563(3)
_cell_length_b                   8.5279(12)
_cell_length_c                   18.464(3)
_cell_measurement_reflns_used    1456
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.35
_cell_measurement_theta_min      2.40
_cell_volume                     2365.4(7)
_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 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker P4'
_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  0.1836
_diffrn_reflns_av_sigmaI/netI    0.1623
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8287
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0732
_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)+(0.0850P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1912
_reflns_number_gt                1255
_reflns_number_total             2711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050391zsi20050808_123956.cif
_cod_data_source_block           7
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2365.4(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4504645
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
N11 N 0.44176(13) 0.3741(3) 0.12219(13) 0.0410(6) Uani 1 1 d .
C12 C 0.40739(16) 0.5000(3) 0.07601(14) 0.0366(7) Uani 1 1 d .
N12 N 0.47089(14) 0.5921(3) 0.06688(12) 0.0372(6) Uani 1 1 d .
H12 H 0.5282(18) 0.548(3) 0.0910(15) 0.045 Uiso 1 1 d .
C13 C 0.31723(16) 0.5313(3) 0.04256(15) 0.0401(7) Uani 1 1 d .
H13 H 0.2938 0.6198 0.0089 0.048 Uiso 1 1 calc R
C14 C 0.26220(17) 0.4311(4) 0.05919(16) 0.0433(8) Uani 1 1 d .
H14 H 0.1999 0.4503 0.0368 0.052 Uiso 1 1 calc R
C15 C 0.29669(17) 0.3035(4) 0.10792(17) 0.0474(8) Uani 1 1 d .
H15 H 0.2597 0.2345 0.1209 0.057 Uiso 1 1 calc R
C16 C 0.38664(18) 0.2800(4) 0.13702(17) 0.0478(8) Uani 1 1 d .
H16 H 0.4111 0.1909 0.1698 0.057 Uiso 1 1 calc R
C17 C 0.46285(18) 0.7422(4) 0.04028(16) 0.0441(8) Uani 1 1 d .
O17 O 0.39262(12) 0.8135(3) 0.01415(13) 0.0614(7) Uani 1 1 d .
C18 C 0.54783(18) 0.8136(4) 0.04631(19) 0.0514(8) Uani 1 1 d .
H18A H 0.5394 0.8544 -0.0060 0.077 Uiso 1 1 calc R
H18B H 0.5947 0.7337 0.0637 0.077 Uiso 1 1 calc R
H18C H 0.5651 0.8994 0.0852 0.077 Uiso 1 1 calc R
C21 C 0.66640(16) 0.3433(4) 0.16828(15) 0.0378(7) Uani 1 1 d .
O21 O 0.60478(12) 0.2528(2) 0.17376(12) 0.0502(6) Uani 1 1 d .
H21 H 0.542(2) 0.312(4) 0.1545(15) 0.060 Uiso 1 1 d .
O22 O 0.65158(11) 0.4759(2) 0.14266(11) 0.0480(6) Uani 1 1 d .
C22 C 0.75429(15) 0.2643(3) 0.19536(16) 0.0386(7) Uani 1 1 d .
H22A H 0.7499 0.1819 0.1561 0.046 Uiso 1 1 calc R
H22B H 0.7673 0.2114 0.2468 0.046 Uiso 1 1 calc R
C23 C 0.83166(14) 0.3695(3) 0.20613(16) 0.0413(7) Uani 1 1 d .
H23A H 0.8387 0.4495 0.2472 0.050 Uiso 1 1 calc R
H23B H 0.8191 0.4247 0.1553 0.050 Uiso 1 1 calc R
C24 C 0.91761(15) 0.2776(3) 0.23116(16) 0.0392(7) Uani 1 1 d .
H24A H 0.9262 0.2147 0.2789 0.047 Uiso 1 1 calc R
H24B H 0.9112 0.2035 0.1878 0.047 Uiso 1 1 calc R
C25 C 1.0000 0.3744(5) 0.2500 0.0454(11) Uani 1 2 d S
H25A H 1.0096 0.4429 0.2962 0.055 Uiso 0.50 1 calc PR
H25B H 0.9904 0.4429 0.2038 0.055 Uiso 0.50 1 calc PR
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 118.1(2) . .
N11 C12 N12 113.1(2) . .
N11 C12 C13 122.0(3) . .
N12 C12 C13 124.9(2) . .
C17 N12 C12 128.1(2) . .
C17 N12 H12 118.1(17) . .
C12 N12 H12 112.8(17) . .
C14 C13 C12 118.3(3) . .
C14 C13 H13 120.9 . .
C12 C13 H13 120.9 . .
C15 C14 C13 120.4(2) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C16 C15 C14 117.2(3) . .
C16 C15 H15 121.4 . .
C14 C15 H15 121.4 . .
N11 C16 C15 124.1(3) . .
N11 C16 H16 118.0 . .
C15 C16 H16 118.0 . .
O17 C17 N12 123.1(3) . .
O17 C17 C18 122.6(3) . .
N12 C17 C18 114.3(2) . .
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 122.8(2) . .
O22 C21 C22 124.3(3) . .
O21 C21 C22 112.9(3) . .
C21 O21 H21 111.9(16) . .
C21 C22 C23 115.6(2) . .
C21 C22 H22A 108.4 . .
C23 C22 H22A 108.4 . .
C21 C22 H22B 108.4 . .
C23 C22 H22B 108.4 . .
H22A C22 H22B 107.4 . .
C22 C23 C24 111.7(2) . .
C22 C23 H23A 109.3 . .
C24 C23 H23A 109.3 . .
C22 C23 H23B 109.3 . .
C24 C23 H23B 109.3 . .
H23A C23 H23B 107.9 . .
C25 C24 C23 115.5(3) . .
C25 C24 H24A 108.4 . .
C23 C24 H24A 108.4 . .
C25 C24 H24B 108.4 . .
C23 C24 H24B 108.4 . .
H24A C24 H24B 107.5 . .
C24 C25 C24 113.5(4) . 2_755
C24 C25 H25A 108.9 . .
C24 C25 H25A 108.9 2_755 .
C24 C25 H25B 108.9 . .
C24 C25 H25B 108.9 2_755 .
H25A C25 H25B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.328(4) .
N11 C12 1.340(3) .
C12 N12 1.378(3) .
C12 C13 1.381(3) .
N12 C17 1.358(4) .
N12 H12 0.94(3) .
C13 C14 1.375(4) .
C13 H13 0.9500 .
C14 C15 1.374(4) .
C14 H14 0.9500 .
C15 C16 1.369(4) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 O17 1.218(3) .
C17 C18 1.494(4) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C21 O22 1.210(3) .
C21 O21 1.317(3) .
C21 C22 1.487(3) .
O21 H21 1.07(3) .
C22 C23 1.508(4) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.516(3) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.505(3) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C24 1.505(3) 2_755
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
O21 H21 N11 1.07(3) 1.60(3) 2.665(3) 171(3)
N12 H12 O22 0.94(3) 1.96(3) 2.893(3) 175(2)
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 N12 177.9(2) .
C16 N11 C12 C13 -1.6(4) .
N11 C12 N12 C17 -163.7(3) .
C13 C12 N12 C17 15.8(4) .
N11 C12 C13 C14 1.5(4) .
N12 C12 C13 C14 -177.9(2) .
C12 C13 C14 C15 0.0(4) .
C13 C14 C15 C16 -1.3(4) .
C12 N11 C16 C15 0.1(4) .
C14 C15 C16 N11 1.3(5) .
C12 N12 C17 O17 -6.1(5) .
C12 N12 C17 C18 173.5(3) .
O22 C21 C22 C23 12.6(4) .
O21 C21 C22 C23 -168.4(2) .
C21 C22 C23 C24 -178.1(2) .
C22 C23 C24 C25 -175.1(2) .
C23 C24 C25 C24 -175.9(3) 2_755
