#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:29:14 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179581 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/46/4504641.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_4504641
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 (C4 H6 O4)
;
_chemical_formula_sum            'C18 H22 N4 O6'
_chemical_formula_weight         390.40
_chemical_name_systematic
;
[N-(2-pyridyl)acetamide]2, succinic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.694(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1172(8)
_cell_length_b                   9.2969(8)
_cell_length_c                   10.6430(9)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.85
_cell_volume                     901.12(13)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9947
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.010(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   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0447
_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          0.1217
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2379
_reflns_number_total             2600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050391zsi20050808_123956.cif
_cod_data_source_block           2
_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_sg_symbol_H-M      P2(1)/n
_cod_database_code               4504641
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.20408(8) 0.47883(9) 0.10927(7) 0.01491(18) Uani 1 1 d .
C12 C 0.07057(9) 0.44681(9) 0.15012(8) 0.01341(19) Uani 1 1 d .
N12 N 0.04706(8) 0.29944(8) 0.16316(7) 0.01507(18) Uani 1 1 d .
H12 H 0.1160(15) 0.2444(16) 0.1385(11) 0.018 Uiso 1 1 d .
C13 C -0.03165(9) 0.55342(10) 0.17581(8) 0.01538(19) Uani 1 1 d .
H13 H -0.1259 0.5287 0.2036 0.018 Uiso 1 1 calc R
C14 C 0.00752(10) 0.69589(10) 0.15987(9) 0.0173(2) Uani 1 1 d .
H14 H -0.0600 0.7704 0.1771 0.021 Uiso 1 1 calc R
C15 C 0.14615(10) 0.72993(10) 0.11844(9) 0.0176(2) Uani 1 1 d .
H15 H 0.1753 0.8271 0.1078 0.021 Uiso 1 1 calc R
C16 C 0.23978(10) 0.61747(10) 0.09339(9) 0.0165(2) Uani 1 1 d .
H16 H 0.3338 0.6394 0.0636 0.020 Uiso 1 1 calc R
C21 C -0.07756(10) 0.23093(10) 0.19938(9) 0.0160(2) Uani 1 1 d .
O21 O -0.18747(8) 0.29350(8) 0.23167(8) 0.02371(19) Uani 1 1 d .
C22 C -0.06709(10) 0.06897(11) 0.19680(10) 0.0207(2) Uani 1 1 d .
H22A H -0.0860 0.0305 0.2802 0.031 Uiso 1 1 calc R
H22B H 0.0315 0.0405 0.1735 0.031 Uiso 1 1 calc R
H22C H -0.1400 0.0307 0.1350 0.031 Uiso 1 1 calc R
C31 C 0.38670(9) 0.16970(11) 0.03516(8) 0.01478(19) Uani 1 1 d .
O31 O 0.41473(8) 0.30832(8) 0.03437(7) 0.01974(18) Uani 1 1 d .
H31 H 0.3360(17) 0.3629(16) 0.0598(14) 0.024 Uiso 1 1 d .
O32 O 0.26939(7) 0.11793(7) 0.06440(7) 0.01849(18) Uani 1 1 d .
C32 C 0.51524(9) 0.08013(9) -0.00181(8) 0.01523(19) Uani 1 1 d .
H32A H 0.6008 0.1019 0.0558 0.018 Uiso 1 1 calc R
H32B H 0.5413 0.1072 -0.0879 0.018 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
C16 N11 C12 118.80(8) . .
N11 C12 N12 113.28(8) . .
N11 C12 C13 121.92(8) . .
N12 C12 C13 124.80(8) . .
C21 N12 C12 128.06(8) . .
C21 N12 H12 115.8(9) . .
C12 N12 H12 115.8(9) . .
C14 C13 C12 118.47(8) . .
C14 C13 H13 120.8 . .
C12 C13 H13 120.8 . .
C13 C14 C15 119.92(8) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C16 C15 C14 117.78(9) . .
C16 C15 H15 121.1 . .
C14 C15 H15 121.1 . .
N11 C16 C15 123.09(8) . .
N11 C16 H16 118.5 . .
C15 C16 H16 118.5 . .
O21 C21 N12 123.94(9) . .
O21 C21 C22 122.25(8) . .
N12 C21 C22 113.81(8) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
O32 C31 O31 123.97(8) . .
O32 C31 C32 123.26(9) . .
O31 C31 C32 112.77(7) . .
C31 O31 H31 112.4(9) . .
C31 C32 C32 113.02(9) . 3_655
C31 C32 H32A 109.0 . .
C32 C32 H32A 109.0 3_655 .
C31 C32 H32B 109.0 . .
C32 C32 H32B 109.0 3_655 .
H32A C32 H32B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.3420(12) .
N11 C12 1.3450(11) .
C12 N12 1.3947(11) .
C12 C13 1.3963(12) .
N12 C21 1.3734(11) .
N12 H12 0.861(14) .
C13 C14 1.3843(13) .
C13 H13 0.9500 .
C14 C15 1.3944(13) .
C14 H14 0.9500 .
C15 C16 1.3836(13) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 O21 1.2219(12) .
C21 C22 1.5091(13) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C31 O32 1.2263(11) .
C31 O31 1.3140(12) .
C31 C32 1.5050(12) .
O31 H31 0.930(16) .
C32 C32 1.5164(18) 3_655
C32 H32A 0.9900 .
C32 H32B 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
O31 H31 N11 0.930(16) 1.716(16) 2.6421(10) 173.7(14)
N12 H12 O32 0.861(14) 2.016(14) 2.8743(10) 174.7(11)
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 -179.80(8) .
C16 N11 C12 C13 0.29(13) .
N11 C12 N12 C21 -178.16(9) .
C13 C12 N12 C21 1.75(15) .
N11 C12 C13 C14 -0.80(13) .
N12 C12 C13 C14 179.30(8) .
C12 C13 C14 C15 0.30(14) .
C13 C14 C15 C16 0.64(14) .
C12 N11 C16 C15 0.75(14) .
C14 C15 C16 N11 -1.21(15) .
C12 N12 C21 O21 -3.41(16) .
C12 N12 C21 C22 176.97(9) .
O32 C31 C32 C32 -0.40(15) 3_655
O31 C31 C32 C32 178.68(9) 3_655
