#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:29:14 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179581 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/46/4504647.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_4504647
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 (C8 H5 N O6)
;
_chemical_formula_sum            'C22 H21 N5 O8'
_chemical_formula_weight         483.44
_chemical_name_systematic
;
N-(3-pyridyl)acetamide, 5-nitroisophthalic 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                 113.382(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.5362(14)
_cell_length_b                   9.3631(7)
_cell_length_c                   12.7665(10)
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.25
_cell_volume                     2143.5(3)
_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 0.939
_diffrn_measured_fraction_theta_max 0.939
_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  0.1106
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7630
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0619
_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          0.1586
_refine_ls_wR_factor_ref         0.1773
_reflns_number_gt                1859
_reflns_number_total             2497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050391zsi20050808_123956.cif
_cod_data_source_block           10
_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      C2/c
_cod_database_code               4504647
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 0.24673(8) 0.47207(16) 0.12999(12) 0.0274(4) Uani 1 1 d . . .
C12 C 0.17514(9) 0.43484(18) 0.09354(13) 0.0234(4) Uani 1 1 d . . .
N12 N 0.16415(8) 0.28799(16) 0.08960(12) 0.0278(4) Uani 1 1 d . A .
H12 H 0.2042(11) 0.236(2) 0.1031(14) 0.033 Uiso 1 1 d . . .
C13 C 0.11852(9) 0.53672(19) 0.06157(13) 0.0260(4) Uani 1 1 d . . .
H13 H 0.0678 0.5086 0.0364 0.031 Uiso 1 1 calc R . .
C14 C 0.13754(10) 0.6792(2) 0.06714(14) 0.0297(4) Uani 1 1 d . . .
H14 H 0.0999 0.7505 0.0454 0.036 Uiso 1 1 calc R . .
C15 C 0.21179(10) 0.7176(2) 0.10452(14) 0.0324(4) Uani 1 1 d . . .
H15 H 0.2260 0.8152 0.1090 0.039 Uiso 1 1 calc R . .
C16 C 0.26448(10) 0.6108(2) 0.13500(15) 0.0308(4) Uani 1 1 d . . .
H16 H 0.3156 0.6365 0.1607 0.037 Uiso 1 1 calc R . .
C21 C 0.09853(10) 0.2157(2) 0.06146(13) 0.0280(4) Uani 1 1 d . . .
O21 O 0.03868(7) 0.27321(14) 0.03984(12) 0.0377(4) Uani 1 1 d . A .
C22A C 0.10620(11) 0.0563(2) 0.05905(18) 0.0380(5) Uani 0.69(2) 1 d P A 1
H22A H 0.0763 0.0208 -0.0179 0.057 Uiso 0.69(2) 1 calc PR A 1
H22B H 0.0886 0.0127 0.1136 0.057 Uiso 0.69(2) 1 calc PR A 1
H22C H 0.1587 0.0314 0.0798 0.057 Uiso 0.69(2) 1 calc PR A 1
C22B C 0.10620(11) 0.0563(2) 0.05905(18) 0.0380(5) Uani 0.31(2) 1 d P A 2
H22D H 0.0609 0.0110 0.0586 0.057 Uiso 0.31(2) 1 calc PR A 2
H22E H 0.1492 0.0254 0.1268 0.057 Uiso 0.31(2) 1 calc PR A 2
H22F H 0.1135 0.0286 -0.0098 0.057 Uiso 0.31(2) 1 calc PR A 2
C31 C 0.43282(9) 0.10661(19) 0.21517(12) 0.0240(4) Uani 1 1 d . . .
O32 O 0.30067(7) 0.11963(14) 0.14266(10) 0.0308(4) Uani 1 1 d . . .
C32 C 0.5000 0.1814(3) 0.2500 0.0247(5) Uani 1 2 d S . .
H32 H 0.5000 0.2829 0.2500 0.030 Uiso 1 2 calc SR . .
O31 O 0.36695(7) 0.32162(14) 0.18781(10) 0.0341(4) Uani 1 1 d . . .
H31 H 0.3155(13) 0.369(2) 0.1628(17) 0.041 Uiso 1 1 d . . .
C35 C 0.5000 -0.1124(3) 0.2500 0.0246(5) Uani 1 2 d S . .
N35 N 0.5000 -0.2686(2) 0.2500 0.0293(5) Uani 1 2 d S . .
C36 C 0.43255(9) -0.04114(19) 0.21440(12) 0.0246(4) Uani 1 1 d . . .
H36 H 0.3870 -0.0926 0.1899 0.029 Uiso 1 1 calc R . .
O36 O 0.44061(8) -0.32987(15) 0.20147(13) 0.0414(4) Uani 1 1 d . . .
C37 C 0.36016(9) 0.18364(19) 0.17838(12) 0.0257(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
C12 N11 C16 119.08(15) . .
N11 C12 N12 113.38(15) . .
N11 C12 C13 121.61(16) . .
N12 C12 C13 125.00(15) . .
C21 N12 C12 127.99(15) . .
C21 N12 H12 116.5(14) . .
C12 N12 H12 115.4(14) . .
C14 C13 C12 118.74(16) . .
C14 C13 H13 120.6 . .
C12 C13 H13 120.6 . .
C13 C14 C15 119.59(17) . .
C13 C14 H14 120.2 . .
C15 C14 H14 120.2 . .
C16 C15 C14 118.23(18) . .
C16 C15 H15 120.9 . .
C14 C15 H15 120.9 . .
N11 C16 C15 122.75(17) . .
N11 C16 H16 118.6 . .
C15 C16 H16 118.6 . .
O21 C21 N12 123.90(17) . .
O21 C21 C22A 122.07(17) . .
N12 C21 C22A 114.03(15) . .
C21 C22A H22A 109.5 . .
C21 C22A H22B 109.5 . .
H22A C22A H22B 109.5 . .
C21 C22A H22C 109.5 . .
H22A C22A H22C 109.5 . .
H22B C22A H22C 109.5 . .
C36 C31 C32 120.30(17) . .
C36 C31 C37 118.73(15) . .
C32 C31 C37 120.97(17) . .
C31 C32 C31 119.8(2) . 2_655
C31 C32 H32 120.1 . .
C31 C32 H32 120.1 2_655 .
C37 O31 H31 110.6(12) . .
C36 C35 C36 122.3(2) 2_655 .
C36 C35 N35 118.83(12) 2_655 .
C36 C35 N35 118.83(12) . .
O36 N35 O36 123.9(2) . 2_655
O36 N35 C35 118.06(11) . .
O36 N35 C35 118.06(11) 2_655 .
C35 C36 C31 118.65(16) . .
C35 C36 H36 120.7 . .
C31 C36 H36 120.7 . .
O32 C37 O31 124.65(16) . .
O32 C37 C31 121.65(16) . .
O31 C37 C31 113.70(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.333(2) .
N11 C16 1.339(2) .
C12 N12 1.389(2) .
C12 C13 1.393(2) .
N12 C21 1.366(2) .
N12 H12 0.88(2) .
C13 C14 1.379(2) .
C13 H13 0.9500 .
C14 C15 1.383(3) .
C14 H14 0.9500 .
C15 C16 1.376(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 O21 1.215(2) .
C21 C22A 1.501(3) .
C22A H22A 0.9800 .
C22A H22B 0.9800 .
C22A H22C 0.9800 .
C31 C36 1.383(2) .
C31 C32 1.396(2) .
C31 C37 1.492(2) .
O32 C37 1.224(2) .
C32 C31 1.396(2) 2_655
C32 H32 0.9500 .
O31 C37 1.299(2) .
O31 H31 1.03(2) .
C35 C36 1.383(2) 2_655
C35 C36 1.383(2) .
C35 N35 1.463(3) .
N35 O36 1.2202(16) .
N35 O36 1.2203(16) 2_655
C36 H36 0.9500 .
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 1.03(2) 1.57(2) 2.5825(19) 168(2)
N12 H12 O32 0.88(2) 2.06(2) 2.936(2) 177.0(18)
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_4
C16 N11 C12 N12 178.44(14) . .
C16 N11 C12 C13 -0.6(2) . .
N11 C12 N12 C21 176.73(15) . .
C13 C12 N12 C21 -4.3(2) . .
N11 C12 C13 C14 0.6(2) . .
N12 C12 C13 C14 -178.33(14) . .
C12 C13 C14 C15 -0.3(2) . .
C13 C14 C15 C16 0.1(2) . .
C12 N11 C16 C15 0.3(2) . .
C14 C15 C16 N11 -0.1(3) . .
C12 N12 C21 O21 -3.4(3) . .
C12 N12 C21 C22A 176.47(15) . .
C36 C31 C32 C31 -0.38(10) . 2_655
C37 C31 C32 C31 179.49(14) . 2_655
C36 C35 N35 O36 -168.26(10) 2_655 .
C36 C35 N35 O36 11.74(10) . .
C36 C35 N35 O36 11.74(10) 2_655 2_655
C36 C35 N35 O36 -168.26(10) . 2_655
C36 C35 C36 C31 -0.38(9) 2_655 .
N35 C35 C36 C31 179.62(9) . .
C32 C31 C36 C35 0.75(19) . .
C37 C31 C36 C35 -179.13(11) . .
C36 C31 C37 O32 -3.6(2) . .
C32 C31 C37 O32 176.57(12) . .
C36 C31 C37 O31 176.71(12) . .
C32 C31 C37 O31 -3.17(19) . .
