#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:29:14 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179581 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/46/4504646.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_4504646
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 (C10 H18 O4)
;
_chemical_formula_sum            'C24 H34 N4 O6'
_chemical_formula_weight         474.55
_chemical_name_systematic
;
[N-(2-pyridyl)acetamide]2, decanedioic 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                92.8090(10)
_cell_angle_beta                 90.2470(10)
_cell_angle_gamma                101.3140(10)
_cell_formula_units_Z            1
_cell_length_a                   5.3767(4)
_cell_length_b                   6.5416(4)
_cell_length_c                   17.0662(12)
_cell_measurement_reflns_used    2744
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.35
_cell_volume                     587.82(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      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6783
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             254
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0466
_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+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                2902
_reflns_number_total             3351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050391zsi20050808_123956.cif
_cod_data_source_block           8
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4504646
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
N11 N 0.39794(17) 0.67116(14) 0.27381(5) 0.0159(2) Uani 1 1 d .
C12 C 0.32841(19) 0.57217(16) 0.33986(6) 0.0141(2) Uani 1 1 d .
N12 N 0.46038(17) 0.41424(14) 0.35354(5) 0.01546(19) Uani 1 1 d .
H12 H 0.574(3) 0.399(2) 0.3184(9) 0.019 Uiso 1 1 d .
C13 C 0.1413(2) 0.62668(16) 0.38883(6) 0.0162(2) Uani 1 1 d .
H13 H 0.0947 0.5547 0.4352 0.019 Uiso 1 1 calc R
C14 C 0.0259(2) 0.78784(17) 0.36814(6) 0.0179(2) Uani 1 1 d .
H14 H -0.1020 0.8274 0.4004 0.022 Uiso 1 1 calc R
C15 C 0.0971(2) 0.89230(17) 0.30004(6) 0.0182(2) Uani 1 1 d .
H15 H 0.0202 1.0036 0.2850 0.022 Uiso 1 1 calc R
C16 C 0.2838(2) 0.82783(17) 0.25509(6) 0.0173(2) Uani 1 1 d .
H16 H 0.3339 0.8980 0.2086 0.021 Uiso 1 1 calc R
C21 C 0.4440(2) 0.28941(16) 0.41642(6) 0.0155(2) Uani 1 1 d .
O21 O 0.29442(16) 0.29321(13) 0.46972(5) 0.0217(2) Uani 1 1 d .
C22 C 0.6312(2) 0.14506(17) 0.41313(6) 0.0179(2) Uani 1 1 d .
H22A H 0.7679 0.1953 0.4516 0.027 Uiso 1 1 calc R
H22B H 0.7026 0.1420 0.3605 0.027 Uiso 1 1 calc R
H22C H 0.5446 0.0041 0.4252 0.027 Uiso 1 1 calc R
C31 C 0.83278(19) 0.43802(16) 0.17258(6) 0.0150(2) Uani 1 1 d .
O31 O 0.71472(15) 0.59424(12) 0.16235(5) 0.01936(19) Uani 1 1 d .
H31 H 0.614(3) 0.611(2) 0.2046(9) 0.023 Uiso 1 1 d .
O32 O 0.80017(16) 0.32836(13) 0.22874(5) 0.0213(2) Uani 1 1 d .
C32 C 1.0091(2) 0.40927(16) 0.10637(6) 0.0161(2) Uani 1 1 d .
H32A H 1.1402 0.5383 0.1042 0.019 Uiso 1 1 calc R
H32B H 0.9109 0.3923 0.0565 0.019 Uiso 1 1 calc R
C33 C 1.1417(2) 0.22519(16) 0.11156(6) 0.0152(2) Uani 1 1 d .
H33A H 1.0137 0.0960 0.1177 0.018 Uiso 1 1 calc R
H33B H 1.2555 0.2471 0.1582 0.018 Uiso 1 1 calc R
C34 C 1.2958(2) 0.20025(16) 0.03807(6) 0.0161(2) Uani 1 1 d .
H34A H 1.4255 0.3291 0.0332 0.019 Uiso 1 1 calc R
H34B H 1.1816 0.1848 -0.0084 0.019 Uiso 1 1 calc R
C35 C 1.42810(19) 0.01381(16) 0.03770(6) 0.0156(2) Uani 1 1 d .
H35A H 1.5484 0.0321 0.0827 0.019 Uiso 1 1 calc R
H35B H 1.2996 -0.1146 0.0448 0.019 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
C16 N11 C12 118.45(9) .
N11 C12 N12 113.38(9) .
N11 C12 C13 122.06(9) .
N12 C12 C13 124.56(9) .
C21 N12 C12 128.48(9) .
C21 N12 H12 116.9(10) .
C12 N12 H12 114.5(10) .
C14 C13 C12 118.41(9) .
C14 C13 H13 120.8 .
C12 C13 H13 120.8 .
C13 C14 C15 120.10(10) .
C13 C14 H14 120.0 .
C15 C14 H14 120.0 .
C16 C15 C14 117.56(10) .
C16 C15 H15 121.2 .
C14 C15 H15 121.2 .
N11 C16 C15 123.43(10) .
N11 C16 H16 118.3 .
C15 C16 H16 118.3 .
O21 C21 N12 124.05(10) .
O21 C21 C22 122.92(9) .
N12 C21 C22 113.03(9) .
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 123.76(9) .
O32 C31 C32 123.89(9) .
O31 C31 C32 112.35(9) .
C31 O31 H31 110.3(9) .
C31 C32 C33 115.60(8) .
C31 C32 H32A 108.4 .
C33 C32 H32A 108.4 .
C31 C32 H32B 108.4 .
C33 C32 H32B 108.4 .
H32A C32 H32B 107.4 .
C32 C33 C34 110.83(8) .
C32 C33 H33A 109.5 .
C34 C33 H33A 109.5 .
C32 C33 H33B 109.5 .
C34 C33 H33B 109.5 .
H33A C33 H33B 108.1 .
C33 C34 C35 113.96(8) .
C33 C34 H34A 108.8 .
C35 C34 H34A 108.8 .
C33 C34 H34B 108.8 .
C35 C34 H34B 108.8 .
H34A C34 H34B 107.7 .
C35 C35 C34 113.14(10) 2_855
C35 C35 H35A 109.0 2_855
C34 C35 H35A 108.9 .
C35 C35 H35B 108.9 2_855
C34 C35 H35B 109.0 .
H35A C35 H35B 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 1.3439(13) .
N11 C12 1.3454(13) .
C12 N12 1.3912(13) .
C12 C13 1.3985(13) .
N12 C21 1.3727(13) .
N12 H12 0.875(15) .
C13 C14 1.3829(14) .
C13 H13 0.9500 .
C14 C15 1.3940(15) .
C14 H14 0.9500 .
C15 C16 1.3839(14) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 O21 1.2195(13) .
C21 C22 1.5086(14) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C31 O32 1.2179(13) .
C31 O31 1.3224(12) .
C31 C32 1.5064(14) .
O31 H31 0.920(16) .
C32 C33 1.5207(14) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.5259(14) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.5274(14) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C35 1.5253(19) 2_855
C35 H35A 0.9900 .
C35 H35B 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 0.920(16) 1.743(16) 2.6538(12) 169.8(14)
N12 H12 O32 0.875(15) 2.050(15) 2.9170(12) 171.2(13)
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 -179.52(9) .
C16 N11 C12 C13 0.37(15) .
N11 C12 N12 C21 177.14(10) .
C13 C12 N12 C21 -2.75(17) .
N11 C12 C13 C14 -0.10(15) .
N12 C12 C13 C14 179.77(10) .
C12 C13 C14 C15 -0.19(16) .
C13 C14 C15 C16 0.21(16) .
C12 N11 C16 C15 -0.35(16) .
C14 C15 C16 N11 0.06(17) .
C12 N12 C21 O21 4.06(18) .
C12 N12 C21 C22 -176.00(10) .
O32 C31 C32 C33 2.31(15) .
O31 C31 C32 C33 -176.86(9) .
C31 C32 C33 C34 174.91(9) .
C32 C33 C34 C35 -178.13(9) .
C33 C34 C35 C35 177.56(11) 2_855
