#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:24:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180077 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/23/7052358.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_7052358
loop_
_publ_author_name
'Christer B. Aakeröy'
'Nate Schultheiss'
'John Desper'
'Curtis Moore'
_publ_section_title
;
 Balancing intermolecular hydrogen-bond interactions for the directed
 assembly of binary 1 : 1 co-crystals
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1452
_journal_paper_doi               10.1039/b608267j
_journal_volume                  30
_journal_year                    2006
_chemical_formula_moiety
;
(C10 H10 N4) (C12 H16 O2)
;
_chemical_formula_sum            'C22 H26 N4 O2'
_chemical_formula_weight         378.47
_chemical_name_systematic
;
2-amino-4-(3-pyridyl)-6-methylpyrimidine, Me5-PhCOOH
;
_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                92.767(5)
_cell_angle_beta                 105.536(4)
_cell_angle_gamma                115.332(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2088(7)
_cell_length_b                   8.7891(6)
_cell_length_c                   15.3371(12)
_cell_measurement_reflns_used    3157
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.60
_cell_volume                     946.59(14)
_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 0.923
_diffrn_measured_fraction_theta_max 0.923
_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  0.0957
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6992
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.040(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.325
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0738
_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          0.1959
_refine_ls_wR_factor_ref         0.2100
_reflns_number_gt                3038
_reflns_number_total             4181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b608267j.txt
_cod_data_source_block           1b
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        946.59(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052358
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.1476(2) 0.0820(2) 0.32892(12) 0.0243(4) Uani 1 1 d . . .
C12 C 0.2724(3) 0.1108(3) 0.41264(14) 0.0247(5) Uani 1 1 d . . .
N12 N 0.4407(3) 0.2506(2) 0.43432(15) 0.0335(5) Uani 1 1 d . . .
H12A H 0.451(4) 0.309(3) 0.390(2) 0.040 Uiso 1 1 d . . .
H12B H 0.521(4) 0.272(3) 0.489(2) 0.040 Uiso 1 1 d . . .
N13 N 0.2410(2) 0.0092(2) 0.47577(12) 0.0256(4) Uani 1 1 d . . .
C14 C 0.0727(3) -0.1317(2) 0.45091(14) 0.0237(4) Uani 1 1 d . . .
C15 C -0.0617(3) -0.1729(3) 0.36498(14) 0.0256(5) Uani 1 1 d . . .
H15 H -0.1786 -0.2752 0.3477 0.031 Uiso 1 1 calc R . .
C16 C -0.0191(3) -0.0592(3) 0.30507(14) 0.0243(5) Uani 1 1 d . . .
C17 C -0.1564(3) -0.0868(3) 0.21294(15) 0.0322(5) Uani 1 1 d . . .
H17A H -0.0910 -0.0682 0.1666 0.048 Uiso 1 1 calc R . .
H17B H -0.2094 -0.0059 0.2138 0.048 Uiso 1 1 calc R . .
H17C H -0.2595 -0.2043 0.1976 0.048 Uiso 1 1 calc R . .
N21 N -0.1715(3) -0.4792(2) 0.57218(13) 0.0316(5) Uani 1 1 d . . .
C22 C -0.1368(3) -0.3740(3) 0.51185(15) 0.0275(5) Uani 1 1 d . . .
H22 H -0.2403 -0.3909 0.4596 0.033 Uiso 1 1 calc R . .
C23 C 0.0409(3) -0.2419(2) 0.52095(14) 0.0240(5) Uani 1 1 d . . .
C24 C -0.0247(3) -0.4524(3) 0.64523(15) 0.0300(5) Uani 1 1 d . . .
H24A H -0.0468 -0.5252 0.6891 0.036 Uiso 1 1 calc R . .
C25 C 0.1575(3) -0.3252(3) 0.66078(15) 0.0310(5) Uani 1 1 d . . .
H25 H 0.2583 -0.3113 0.7137 0.037 Uiso 1 1 calc R . .
C26 C 0.1903(3) -0.2181(3) 0.59754(15) 0.0288(5) Uani 1 1 d . . .
H26 H 0.3145 -0.1289 0.6066 0.035 Uiso 1 1 calc R . .
C31 C 0.3270(3) 0.5442(2) 0.15974(14) 0.0235(5) Uani 1 1 d . . .
C32 C 0.3530(3) 0.7051(2) 0.19548(14) 0.0241(5) Uani 1 1 d . . .
C33 C 0.3291(3) 0.8133(3) 0.13465(15) 0.0255(5) Uani 1 1 d . . .
C34 C 0.2756(3) 0.7574(3) 0.03965(15) 0.0264(5) Uani 1 1 d . A .
C35 C 0.2540(3) 0.5972(3) 0.00514(14) 0.0269(5) Uani 1 1 d . . .
C36 C 0.2805(3) 0.4897(3) 0.06568(14) 0.0248(5) Uani 1 1 d . A .
C41 C 0.3430(3) 0.4252(3) 0.22508(14) 0.0250(5) Uani 1 1 d . . .
O41 O 0.1778(2) 0.29712(18) 0.21647(10) 0.0298(4) Uani 1 1 d . . .
H41 H 0.191(4) 0.236(3) 0.2606(19) 0.036 Uiso 1 1 d . . .
O42 O 0.4916(2) 0.4468(2) 0.27978(11) 0.0368(4) Uani 1 1 d . . .
C42 C 0.4084(3) 0.7618(3) 0.29813(15) 0.0320(5) Uani 1 1 d . . .
H42A H 0.3849 0.6620 0.3282 0.048 Uiso 1 1 calc R . .
H42B H 0.3326 0.8161 0.3106 0.048 Uiso 1 1 calc R . .
H42C H 0.5438 0.8440 0.3223 0.048 Uiso 1 1 calc R . .
C43 C 0.3603(4) 0.9885(3) 0.17156(17) 0.0356(6) Uani 1 1 d . . .
H43A H 0.4432 1.0736 0.1435 0.053 Uiso 1 1 calc R . .
H43B H 0.4204 1.0152 0.2386 0.053 Uiso 1 1 calc R . .
H43C H 0.2377 0.9908 0.1567 0.053 Uiso 1 1 calc R . .
C44 C 0.2404(3) 0.8696(3) -0.02666(17) 0.0362(6) Uani 1 1 d . . .
H44A H 0.3429 0.9134 -0.0541 0.054 Uiso 1 1 calc R A .
H44B H 0.2371 0.9659 0.0064 0.054 Uiso 1 1 calc R . .
H44C H 0.1185 0.8024 -0.0754 0.054 Uiso 1 1 calc R . .
C45A C 0.1976(4) 0.5370(3) -0.09679(15) 0.0362(6) Uani 0.51(3) 1 d P A 1
H45A H 0.0936 0.4197 -0.1145 0.054 Uiso 0.51(3) 1 calc PR A 1
H45B H 0.3070 0.5394 -0.1122 0.054 Uiso 0.51(3) 1 calc PR A 1
H45C H 0.1553 0.6127 -0.1302 0.054 Uiso 0.51(3) 1 calc PR A 1
C45B C 0.1976(4) 0.5370(3) -0.09679(15) 0.0362(6) Uani 0.49(3) 1 d P A 2
H45D H 0.0626 0.5052 -0.1254 0.054 Uiso 0.49(3) 1 calc PR A 2
H45E H 0.2189 0.4372 -0.1076 0.054 Uiso 0.49(3) 1 calc PR A 2
H45F H 0.2744 0.6293 -0.1237 0.054 Uiso 0.49(3) 1 calc PR A 2
C46 C 0.2629(3) 0.3191(3) 0.02917(16) 0.0333(5) Uani 1 1 d . . .
H46A H 0.3486 0.3364 -0.0074 0.050 Uiso 1 1 calc R A .
H46B H 0.1315 0.2446 -0.0096 0.050 Uiso 1 1 calc R . .
H46C H 0.2974 0.2654 0.0808 0.050 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
_geom_angle_publ_flag
C16 N11 C12 117.98(16) . . ?
N12 C12 N11 117.10(17) . . ?
N12 C12 N13 117.95(19) . . ?
N11 C12 N13 124.96(18) . . ?
C12 N12 H12A 112.7(18) . . ?
C12 N12 H12B 117.6(18) . . ?
H12A N12 H12B 130(3) . . ?
C14 N13 C12 116.33(18) . . ?
N13 C14 C15 122.26(17) . . ?
N13 C14 C23 115.59(18) . . ?
C15 C14 C23 122.15(18) . . ?
C14 C15 C16 117.52(19) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
N11 C16 C15 120.92(19) . . ?
N11 C16 C17 117.07(16) . . ?
C15 C16 C17 122.00(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C24 N21 C22 116.95(18) . . ?
N21 C22 C23 124.0(2) . . ?
N21 C22 H22 118.0 . . ?
C23 C22 H22 118.0 . . ?
C26 C23 C22 117.46(18) . . ?
C26 C23 C14 120.63(18) . . ?
C22 C23 C14 121.90(19) . . ?
N21 C24 C25 123.69(19) . . ?
N21 C24 H24A 118.2 . . ?
C25 C24 H24A 118.2 . . ?
C24 C25 C26 118.4(2) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C23 119.5(2) . . ?
C25 C26 H26 120.3 . . ?
C23 C26 H26 120.3 . . ?
C36 C31 C32 121.83(18) . . ?
C36 C31 C41 119.61(18) . . ?
C32 C31 C41 118.52(18) . . ?
C31 C32 C33 118.85(19) . . ?
C31 C32 C42 120.37(17) . . ?
C33 C32 C42 120.77(19) . . ?
C32 C33 C34 119.80(19) . . ?
C32 C33 C43 119.87(19) . . ?
C34 C33 C43 120.33(18) . . ?
C35 C34 C33 120.56(18) . . ?
C35 C34 C44 119.3(2) . . ?
C33 C34 C44 120.2(2) . . ?
C36 C35 C34 119.83(19) . . ?
C36 C35 C45A 119.4(2) . . ?
C34 C35 C45A 120.75(18) . . ?
C31 C36 C35 119.05(19) . . ?
C31 C36 C46 120.84(18) . . ?
C35 C36 C46 120.09(19) . . ?
O42 C41 O41 124.09(18) . . ?
O42 C41 C31 123.80(17) . . ?
O41 C41 C31 112.11(17) . . ?
C41 O41 H41 109.6(17) . . ?
C32 C42 H42A 109.5 . . ?
C32 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C32 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C33 C43 H43A 109.5 . . ?
C33 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C33 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C34 C44 H44A 109.5 . . ?
C34 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C34 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C35 C45A H45A 109.5 . . ?
C35 C45A H45B 109.5 . . ?
C35 C45A H45C 109.5 . . ?
C36 C46 H46A 109.5 . . ?
C36 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C36 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.335(3) . ?
N11 C12 1.343(3) . ?
C12 N12 1.338(3) . ?
C12 N13 1.350(2) . ?
N12 H12A 0.87(3) . ?
N12 H12B 0.88(3) . ?
N13 C14 1.340(3) . ?
C14 C15 1.385(3) . ?
C14 C23 1.482(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.485(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 C24 1.331(3) . ?
N21 C22 1.338(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C26 1.383(3) . ?
C24 C25 1.377(3) . ?
C24 H24A 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.392(3) . ?
C31 C32 1.397(3) . ?
C31 C41 1.505(3) . ?
C32 C33 1.400(3) . ?
C32 C42 1.510(3) . ?
C33 C34 1.400(3) . ?
C33 C43 1.503(3) . ?
C34 C35 1.399(3) . ?
C34 C44 1.508(3) . ?
C35 C36 1.398(3) . ?
C35 C45A 1.504(3) . ?
C36 C46 1.508(3) . ?
C41 O42 1.211(3) . ?
C41 O41 1.306(2) . ?
O41 H41 0.90(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45A H45A 0.9800 . ?
C45A H45B 0.9800 . ?
C45A H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
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
O41 H41 N11 0.90(3) 1.72(3) 2.599(2) 164(3) .
N12 H12A O42 0.87(3) 2.15(3) 3.013(2) 176(3) .
N12 H12B N21 0.88(3) 2.46(3) 3.112(3) 132(2) 1_665
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 N12 178.2(2) . . . . ?
C16 N11 C12 N13 -1.4(3) . . . . ?
N12 C12 N13 C14 -178.50(19) . . . . ?
N11 C12 N13 C14 1.1(3) . . . . ?
C12 N13 C14 C15 0.7(3) . . . . ?
C12 N13 C14 C23 179.84(18) . . . . ?
N13 C14 C15 C16 -2.1(3) . . . . ?
C23 C14 C15 C16 178.82(19) . . . . ?
C12 N11 C16 C15 -0.1(3) . . . . ?
C12 N11 C16 C17 178.8(2) . . . . ?
C14 C15 C16 N11 1.8(3) . . . . ?
C14 C15 C16 C17 -177.2(2) . . . . ?
C24 N21 C22 C23 0.5(3) . . . . ?
N21 C22 C23 C26 -0.3(3) . . . . ?
N21 C22 C23 C14 178.4(2) . . . . ?
N13 C14 C23 C26 -13.0(3) . . . . ?
C15 C14 C23 C26 166.1(2) . . . . ?
N13 C14 C23 C22 168.31(19) . . . . ?
C15 C14 C23 C22 -12.5(3) . . . . ?
C22 N21 C24 C25 -0.6(3) . . . . ?
N21 C24 C25 C26 0.5(4) . . . . ?
C24 C25 C26 C23 -0.2(3) . . . . ?
C22 C23 C26 C25 0.1(3) . . . . ?
C14 C23 C26 C25 -178.6(2) . . . . ?
C36 C31 C32 C33 0.8(3) . . . . ?
C41 C31 C32 C33 -176.90(17) . . . . ?
C36 C31 C32 C42 -178.40(19) . . . . ?
C41 C31 C32 C42 3.9(3) . . . . ?
C31 C32 C33 C34 1.5(3) . . . . ?
C42 C32 C33 C34 -179.30(18) . . . . ?
C31 C32 C33 C43 -178.70(18) . . . . ?
C42 C32 C33 C43 0.5(3) . . . . ?
C32 C33 C34 C35 -2.9(3) . . . . ?
C43 C33 C34 C35 177.38(19) . . . . ?
C32 C33 C34 C44 177.05(18) . . . . ?
C43 C33 C34 C44 -2.7(3) . . . . ?
C33 C34 C35 C36 1.9(3) . . . . ?
C44 C34 C35 C36 -178.04(19) . . . . ?
C33 C34 C35 C45A -179.68(19) . . . . ?
C44 C34 C35 C45A 0.4(3) . . . . ?
C32 C31 C36 C35 -1.7(3) . . . . ?
C41 C31 C36 C35 175.89(18) . . . . ?
C32 C31 C36 C46 176.88(19) . . . . ?
C41 C31 C36 C46 -5.5(3) . . . . ?
C34 C35 C36 C31 0.4(3) . . . . ?
C45A C35 C36 C31 -178.06(18) . . . . ?
C34 C35 C36 C46 -178.22(18) . . . . ?
C45A C35 C36 C46 3.3(3) . . . . ?
C36 C31 C41 O42 110.8(3) . . . . ?
C32 C31 C41 O42 -71.4(3) . . . . ?
C36 C31 C41 O41 -69.8(3) . . . . ?
C32 C31 C41 O41 107.9(2) . . . . ?
