#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/23/7052360.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_7052360
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
;
(C11 H12 N4 O) (C9 H11 N O2)
;
_chemical_formula_sum            'C20 H23 N5 O3'
_chemical_formula_weight         381.43
_chemical_name_systematic
;
2-amino-4-(6-methoxy-3-pyridyl)-6-methylpyrimidine, 4-(Me2N)-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                101.607(2)
_cell_angle_beta                 90.830(2)
_cell_angle_gamma                106.753(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8442(12)
_cell_length_b                   8.8879(14)
_cell_length_c                   14.216(2)
_cell_measurement_reflns_used    4307
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.55
_cell_volume                     926.9(2)
_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 0.930
_diffrn_measured_fraction_theta_max 0.930
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8262
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_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          0.1234
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                3502
_reflns_number_total             4281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b608267j.txt
_cod_data_source_block           2a
_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        926.8(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052360
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 0.42238(14) 0.12732(12) 0.58482(7) 0.0158(2) Uani 1 1 d . . .
C12 C 0.36051(16) 0.14813(15) 0.50048(9) 0.0155(3) Uani 1 1 d . . .
N12 N 0.44299(15) 0.28617(13) 0.47346(8) 0.0181(2) Uani 1 1 d . . .
H12A H 0.524(2) 0.3614(19) 0.5161(11) 0.022 Uiso 1 1 d . . .
H12B H 0.388(2) 0.3135(19) 0.4298(12) 0.022 Uiso 1 1 d . . .
N13 N 0.22700(14) 0.04061(12) 0.44035(7) 0.0161(2) Uani 1 1 d . . .
C14 C 0.15049(16) -0.09867(15) 0.46628(9) 0.0153(3) Uani 1 1 d . . .
C15 C 0.20431(17) -0.12992(15) 0.55274(9) 0.0171(3) Uani 1 1 d . . .
H15 H 0.1476 -0.2282 0.5713 0.020 Uiso 1 1 calc R . .
C16 C 0.34302(17) -0.01278(15) 0.61044(9) 0.0165(3) Uani 1 1 d . . .
C17 C 0.41644(18) -0.03350(15) 0.70318(9) 0.0197(3) Uani 1 1 d . . .
H17A H 0.3432 -0.1341 0.7183 0.030 Uiso 1 1 calc R . .
H17B H 0.4147 0.0571 0.7550 0.030 Uiso 1 1 calc R . .
H17C H 0.5395 -0.0371 0.6969 0.030 Uiso 1 1 calc R . .
N21 N -0.15470(15) -0.28647(13) 0.24089(8) 0.0191(2) Uani 1 1 d . . .
C22 C -0.02900(17) -0.18637(15) 0.30872(9) 0.0178(3) Uani 1 1 d . . .
H22 H 0.0396 -0.0874 0.2949 0.021 Uiso 1 1 calc R . .
C23 C 0.00733(17) -0.21787(15) 0.39758(9) 0.0156(3) Uani 1 1 d . . .
C24 C -0.09508(17) -0.36445(15) 0.41707(9) 0.0178(3) Uani 1 1 d . . .
H24 H -0.0755 -0.3912 0.4769 0.021 Uiso 1 1 calc R . .
C25 C -0.22379(18) -0.46908(15) 0.34908(9) 0.0191(3) Uani 1 1 d . . .
H25 H -0.2944 -0.5691 0.3607 0.023 Uiso 1 1 calc R . .
C26 C -0.24779(17) -0.42384(15) 0.26201(9) 0.0176(3) Uani 1 1 d . . .
O26 O -0.37651(13) -0.52974(11) 0.19709(7) 0.0222(2) Uani 1 1 d . . .
C27 C -0.4072(2) -0.48007(17) 0.11040(10) 0.0258(3) Uani 1 1 d . . .
H27A H -0.4385 -0.3793 0.1264 0.039 Uiso 1 1 calc R . .
H27B H -0.5055 -0.5634 0.0699 0.039 Uiso 1 1 calc R . .
H27C H -0.2988 -0.4635 0.0755 0.039 Uiso 1 1 calc R . .
C31 C 0.85476(17) 0.59744(15) 0.77728(9) 0.0175(3) Uani 1 1 d . . .
C37 C 0.73317(17) 0.48082(15) 0.69820(9) 0.0175(3) Uani 1 1 d . . .
O31 O 0.65792(13) 0.33820(11) 0.71663(7) 0.0202(2) Uani 1 1 d . . .
H31 H 0.580(2) 0.2675(19) 0.6638(11) 0.024 Uiso 1 1 d . . .
O32 O 0.70584(13) 0.51508(11) 0.62062(7) 0.0237(2) Uani 1 1 d . . .
C32 C 0.93250(18) 0.75660(16) 0.76885(9) 0.0187(3) Uani 1 1 d . . .
H32 H 0.9063 0.7886 0.7118 0.022 Uiso 1 1 calc R . .
C33 C 1.04641(18) 0.86788(15) 0.84174(9) 0.0193(3) Uani 1 1 d . . .
H33 H 1.0972 0.9751 0.8342 0.023 Uiso 1 1 calc R . .
C34 C 1.08863(18) 0.82451(15) 0.92749(9) 0.0198(3) Uani 1 1 d . . .
N34 N 1.19760(18) 0.93360(14) 1.00186(8) 0.0270(3) Uani 1 1 d . . .
C38 C 1.2963(2) 1.09336(16) 0.99025(10) 0.0264(3) Uani 1 1 d . . .
H38A H 1.3700 1.0845 0.9355 0.040 Uiso 1 1 calc R . .
H38B H 1.3731 1.1518 1.0490 0.040 Uiso 1 1 calc R . .
H38C H 1.2123 1.1517 0.9784 0.040 Uiso 1 1 calc R . .
C39 C 1.2315(2) 0.88689(17) 1.09071(10) 0.0247(3) Uani 1 1 d . . .
H39A H 1.1178 0.8342 1.1144 0.037 Uiso 1 1 calc R . .
H39B H 1.2964 0.9827 1.1390 0.037 Uiso 1 1 calc R . .
H39C H 1.3034 0.8122 1.0787 0.037 Uiso 1 1 calc R . .
C35 C 1.01044(19) 0.66332(16) 0.93508(9) 0.0213(3) Uani 1 1 d . . .
H35 H 1.0367 0.6300 0.9916 0.026 Uiso 1 1 calc R . .
C36 C 0.89639(19) 0.55350(16) 0.86142(10) 0.0206(3) Uani 1 1 d . . .
H36 H 0.8453 0.4459 0.8683 0.025 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 117.03(11) . . ?
N13 C12 N12 117.43(11) . . ?
N13 C12 N11 125.44(11) . . ?
N12 C12 N11 117.10(11) . . ?
C12 N12 H12A 117.1(10) . . ?
C12 N12 H12B 117.8(11) . . ?
H12A N12 H12B 120.1(15) . . ?
C14 N13 C12 116.88(10) . . ?
N13 C14 C15 121.63(11) . . ?
N13 C14 C23 116.12(11) . . ?
C15 C14 C23 122.25(11) . . ?
C16 C15 C14 117.78(11) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
N11 C16 C15 121.23(11) . . ?
N11 C16 C17 115.80(11) . . ?
C15 C16 C17 122.96(11) . . ?
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 . . ?
C26 N21 C22 116.40(11) . . ?
N21 C22 C23 124.56(12) . . ?
N21 C22 H22 117.7 . . ?
C23 C22 H22 117.7 . . ?
C22 C23 C24 117.09(11) . . ?
C22 C23 C14 119.68(11) . . ?
C24 C23 C14 123.23(11) . . ?
C25 C24 C23 119.60(12) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 118.02(12) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
N21 C26 O26 119.42(11) . . ?
N21 C26 C25 124.33(12) . . ?
O26 C26 C25 116.25(11) . . ?
C26 O26 C27 116.24(10) . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C36 C31 C32 118.18(12) . . ?
C36 C31 C37 121.64(11) . . ?
C32 C31 C37 120.18(11) . . ?
O32 C37 O31 122.88(12) . . ?
O32 C37 C31 122.15(11) . . ?
O31 C37 C31 114.96(11) . . ?
C37 O31 H31 111.9(9) . . ?
C33 C32 C31 121.30(12) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 120.88(12) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
N34 C34 C33 122.02(12) . . ?
N34 C34 C35 120.55(12) . . ?
C33 C34 C35 117.42(12) . . ?
C34 N34 C39 120.61(11) . . ?
C34 N34 C38 120.83(11) . . ?
C39 N34 C38 118.25(11) . . ?
N34 C38 H38A 109.5 . . ?
N34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N34 C39 H39A 109.5 . . ?
N34 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N34 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C36 C35 C34 120.93(12) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C31 121.29(12) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
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 1.3464(16) . ?
N11 C12 1.3533(15) . ?
C12 N13 1.3451(16) . ?
C12 N12 1.3456(16) . ?
N12 H12A 0.894(17) . ?
N12 H12B 0.862(16) . ?
N13 C14 1.3380(16) . ?
C14 C15 1.3986(17) . ?
C14 C23 1.4843(17) . ?
C15 C16 1.3849(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.4968(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N21 C26 1.3244(17) . ?
N21 C22 1.3472(16) . ?
C22 C23 1.3905(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.4027(17) . ?
C24 C25 1.3737(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.4023(18) . ?
C25 H25 0.9500 . ?
C26 O26 1.3538(15) . ?
O26 C27 1.4295(15) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C31 C36 1.3928(17) . ?
C31 C32 1.4001(17) . ?
C31 C37 1.4759(17) . ?
C37 O32 1.2332(15) . ?
C37 O31 1.3155(15) . ?
O31 H31 0.951(17) . ?
C32 C33 1.3789(18) . ?
C32 H32 0.9500 . ?
C33 C34 1.4125(17) . ?
C33 H33 0.9500 . ?
C34 N34 1.3683(17) . ?
C34 C35 1.4135(18) . ?
N34 C39 1.4504(17) . ?
N34 C38 1.4515(17) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C35 C36 1.3812(18) . ?
C35 H35 0.9500 . ?
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
_geom_hbond_site_symmetry_A
O31 H31 N11 0.951(17) 1.690(17) 2.6321(14) 170.0(15) .
N12 H12A O32 0.894(17) 2.026(17) 2.9173(15) 174.3(14) .
N12 H12B O32 0.862(16) 2.110(16) 2.8925(15) 150.8(14) 2_666
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 N13 -0.12(18) . . . . ?
C16 N11 C12 N12 -178.18(11) . . . . ?
N12 C12 N13 C14 177.57(11) . . . . ?
N11 C12 N13 C14 -0.48(18) . . . . ?
C12 N13 C14 C15 1.21(17) . . . . ?
C12 N13 C14 C23 -178.13(10) . . . . ?
N13 C14 C15 C16 -1.33(18) . . . . ?
C23 C14 C15 C16 177.97(11) . . . . ?
C12 N11 C16 C15 0.00(18) . . . . ?
C12 N11 C16 C17 178.96(10) . . . . ?
C14 C15 C16 N11 0.69(18) . . . . ?
C14 C15 C16 C17 -178.19(11) . . . . ?
C26 N21 C22 C23 -0.24(19) . . . . ?
N21 C22 C23 C24 -0.05(19) . . . . ?
N21 C22 C23 C14 179.47(11) . . . . ?
N13 C14 C23 C22 5.40(17) . . . . ?
C15 C14 C23 C22 -173.93(11) . . . . ?
N13 C14 C23 C24 -175.10(11) . . . . ?
C15 C14 C23 C24 5.56(19) . . . . ?
C22 C23 C24 C25 0.26(18) . . . . ?
C14 C23 C24 C25 -179.25(11) . . . . ?
C23 C24 C25 C26 -0.18(19) . . . . ?
C22 N21 C26 O26 179.84(11) . . . . ?
C22 N21 C26 C25 0.33(19) . . . . ?
C24 C25 C26 N21 -0.1(2) . . . . ?
C24 C25 C26 O26 -179.65(11) . . . . ?
N21 C26 O26 C27 -2.65(18) . . . . ?
C25 C26 O26 C27 176.89(11) . . . . ?
C36 C31 C37 O32 -174.46(12) . . . . ?
C32 C31 C37 O32 5.17(19) . . . . ?
C36 C31 C37 O31 5.05(18) . . . . ?
C32 C31 C37 O31 -175.32(11) . . . . ?
C36 C31 C32 C33 -0.4(2) . . . . ?
C37 C31 C32 C33 179.95(12) . . . . ?
C31 C32 C33 C34 0.1(2) . . . . ?
C32 C33 C34 N34 -178.29(13) . . . . ?
C32 C33 C34 C35 0.3(2) . . . . ?
C33 C34 N34 C39 177.08(12) . . . . ?
C35 C34 N34 C39 -1.5(2) . . . . ?
C33 C34 N34 C38 -9.4(2) . . . . ?
C35 C34 N34 C38 172.09(13) . . . . ?
N34 C34 C35 C36 178.20(13) . . . . ?
C33 C34 C35 C36 -0.4(2) . . . . ?
C34 C35 C36 C31 0.1(2) . . . . ?
C32 C31 C36 C35 0.3(2) . . . . ?
C37 C31 C36 C35 179.94(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141716
