#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:58:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180458 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/27/7212755.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_7212755
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Rajbanshi, Arbin'
'Li, Z. Jane'
'Desper, John'
_publ_section_title
;
 Mapping out the synthetic landscape for re-crystallization,
 co-crystallization and salt formation
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4231
_journal_paper_doi               10.1039/c0ce00052c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety
;
(C5 H6 N2)2 (C10 H18 O4)
;
_chemical_formula_sum            'C20 H30 N4 O4'
_chemical_formula_weight         390.48
_chemical_name_systematic
;
AR-1g-15 2-aminopyridine, HOOC-(CH2)8-COOH
;
_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                 102.979(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2382(6)
_cell_length_b                   7.3603(5)
_cell_length_c                   17.7902(11)
_cell_measurement_reflns_used    6851
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.65
_cell_measurement_theta_min      2.55
_cell_volume                     1051.16(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12489
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         31.51
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0400
_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)+(0.0600P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2982
_reflns_number_total             3494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00052c.txt
_cod_data_source_block           ar0816m(A15)
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7212755
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 0.51614(9) -0.07936(9) 0.15436(4) 0.01800(15) Uani 1 1 d .
H11 H 0.4781(14) 0.0339(16) 0.1236(6) 0.022 Uiso 1 1 d .
C12 C 0.47027(10) -0.11222(11) 0.22143(4) 0.01764(16) Uani 1 1 d .
N12 N 0.38003(10) 0.01187(11) 0.24821(4) 0.02457(17) Uani 1 1 d .
H12A H 0.3459(16) 0.1148(18) 0.2202(7) 0.029 Uiso 1 1 d .
H12B H 0.3319(16) -0.0220(17) 0.2867(7) 0.029 Uiso 1 1 d .
C13 C 0.52001(11) -0.27795(12) 0.26048(5) 0.02085(17) Uani 1 1 d .
H13 H 0.4902 -0.3039 0.3079 0.025 Uiso 1 1 calc R
C14 C 0.61116(11) -0.39994(13) 0.22934(5) 0.02457(18) Uani 1 1 d .
H14 H 0.6438 -0.5116 0.2551 0.029 Uiso 1 1 calc R
C15 C 0.65714(12) -0.36194(13) 0.15945(5) 0.02585(19) Uani 1 1 d .
H15 H 0.7218 -0.4457 0.1379 0.031 Uiso 1 1 calc R
C16 C 0.60623(11) -0.20117(12) 0.12352(5) 0.02190(17) Uani 1 1 d .
H16 H 0.6346 -0.1741 0.0758 0.026 Uiso 1 1 calc R
C21 C 0.33195(10) 0.32043(11) 0.08966(4) 0.01750(16) Uani 1 1 d .
O21 O 0.42415(9) 0.20129(9) 0.06861(4) 0.02556(16) Uani 1 1 d .
O22 O 0.28338(9) 0.31475(8) 0.15118(3) 0.02385(15) Uani 1 1 d .
C22 C 0.27704(10) 0.47603(11) 0.03385(4) 0.01772(15) Uani 1 1 d .
H22A H 0.2064 0.4261 -0.0142 0.021 Uiso 1 1 calc R
H22B H 0.3772 0.5294 0.0204 0.021 Uiso 1 1 calc R
C23 C 0.18138(10) 0.62718(10) 0.06281(4) 0.01736(15) Uani 1 1 d .
H23A H 0.2516 0.6797 0.1104 0.021 Uiso 1 1 calc R
H23B H 0.0804 0.5756 0.0761 0.021 Uiso 1 1 calc R
C24 C 0.13022(11) 0.77744(11) 0.00329(5) 0.01939(16) Uani 1 1 d .
H24A H 0.2315 0.8300 -0.0093 0.023 Uiso 1 1 calc R
H24B H 0.0619 0.7241 -0.0446 0.023 Uiso 1 1 calc R
C25 C 0.03165(11) 0.92866(11) 0.03081(5) 0.02013(16) Uani 1 1 d .
H25A H 0.1033 0.9886 0.0762 0.024 Uiso 1 1 calc R
H25B H -0.0646 0.8748 0.0475 0.024 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
C12 N11 C16 121.71(7) . .
C12 N11 H11 120.8(6) . .
C16 N11 H11 117.3(6) . .
N12 C12 N11 118.83(7) . .
N12 C12 C13 122.54(7) . .
N11 C12 C13 118.63(7) . .
C12 N12 H12A 120.1(8) . .
C12 N12 H12B 117.3(8) . .
H12A N12 H12B 120.6(11) . .
C14 C13 C12 119.45(7) . .
C14 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
C13 C14 C15 120.64(8) . .
C13 C14 H14 119.7 . .
C15 C14 H14 119.7 . .
C16 C15 C14 118.08(8) . .
C16 C15 H15 121.0 . .
C14 C15 H15 121.0 . .
N11 C16 C15 121.47(8) . .
N11 C16 H16 119.3 . .
C15 C16 H16 119.3 . .
O22 C21 O21 124.49(7) . .
O22 C21 C22 119.50(7) . .
O21 C21 C22 115.99(7) . .
C21 C22 C23 115.61(6) . .
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 112.31(6) . .
C22 C23 H23A 109.1 . .
C24 C23 H23A 109.1 . .
C22 C23 H23B 109.1 . .
C24 C23 H23B 109.1 . .
H23A C23 H23B 107.9 . .
C25 C24 C23 113.05(7) . .
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 113.20(8) . 3_575
C24 C25 H25A 108.9 . .
C25 C25 H25A 108.9 3_575 .
C24 C25 H25B 108.9 . .
C25 C25 H25B 108.9 3_575 .
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
N11 C12 1.3519(10) .
N11 C16 1.3560(11) .
N11 H11 1.007(12) .
C12 N12 1.3315(11) .
C12 C13 1.4179(11) .
N12 H12A 0.915(13) .
N12 H12B 0.901(13) .
C13 C14 1.3653(12) .
C13 H13 0.9500 .
C14 C15 1.4068(13) .
C14 H14 0.9500 .
C15 C16 1.3654(12) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 O22 1.2474(10) .
C21 O21 1.2704(10) .
C21 C22 1.5168(11) .
C22 C23 1.5187(11) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.5236(11) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.5220(11) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C25 1.5230(16) 3_575
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
N11 H11 O21 1.007(12) 1.574(12) 2.5786(9) 174.3(10) .
N12 H12A O22 0.915(13) 1.912(14) 2.8224(10) 172.7(12) .
N12 H12B O22 0.901(13) 2.009(13) 2.8641(10) 158.0(11) 2_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_4
C16 N11 C12 N12 -179.15(8) .
C16 N11 C12 C13 0.73(12) .
N12 C12 C13 C14 179.37(8) .
N11 C12 C13 C14 -0.51(12) .
C12 C13 C14 C15 0.56(14) .
C13 C14 C15 C16 -0.80(14) .
C12 N11 C16 C15 -1.02(13) .
C14 C15 C16 N11 1.02(14) .
O22 C21 C22 C23 7.04(11) .
O21 C21 C22 C23 -174.17(7) .
C21 C22 C23 C24 -179.74(7) .
C22 C23 C24 C25 179.04(7) .
C23 C24 C25 C25 -175.37(8) 3_575
