#------------------------------------------------------------------------------
#$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $
#$Revision: 91932 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/27/1502729.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_1502729
loop_
_publ_author_name
'O\'smia\/lowski, Borys'
'Kolehmainen, Erkki'
'Dobosz, Robert'
'Gawinecki, Ryszard'
'Kauppinen, Reijo'
'Valkonen, Arto'
'Koivukorpi, Juha'
'Rissanen, Kari'
_publ_section_title
;
 Self-organization of 2-acylaminopyridines in the solid state and in
 solution.
;
_journal_issue                   38
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              10421
_journal_page_last               10426
_journal_volume                  114
_journal_year                    2010
_chemical_formula_moiety         'C11 H16 N2 O'
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0135(2)
_cell_length_b                   10.1491(2)
_cell_length_c                   19.8528(3)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_cell_volume                     2219.09(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2008)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w 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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4761
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0401
_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/[\s^2^(Fo^2^)+(0.0432P)^2^+0.9526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2224
_reflns_number_total             2549
_reflns_threshold_expression     >2\s(I)
_[local]_cod_data_source_file    jp1063116_si_009.cif
_[local]_cod_data_source_block   meptbu
_[local]_cod_cif_authors_sg_H-M  Pbca
_cod_database_code               1502729
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
O8 O 0.74237(8) 0.90486(7) 0.65261(4) 0.0249(2) Uani 1 1 d .
N1 N 0.51999(8) 0.59583(9) 0.59563(5) 0.0201(2) Uani 1 1 d .
N7 N 0.69291(9) 0.68979(9) 0.63780(5) 0.0201(2) Uani 1 1 d D
H7 H 0.7057(13) 0.6067(12) 0.6491(7) 0.024 Uiso 1 1 d D
C2 C 0.58867(10) 0.70442(11) 0.59722(5) 0.0180(2) Uani 1 1 d .
C3 C 0.56134(10) 0.81890(11) 0.56158(6) 0.0219(2) Uani 1 1 d .
H3 H 0.6122 0.8944 0.5637 0.026 Uiso 1 1 calc R
C4 C 0.45667(11) 0.81788(12) 0.52284(6) 0.0281(3) Uani 1 1 d .
H4 H 0.4348 0.8937 0.4976 0.034 Uiso 1 1 calc R
C5 C 0.38409(11) 0.70702(13) 0.52081(6) 0.0293(3) Uani 1 1 d .
H5 H 0.3122 0.7057 0.4944 0.035 Uiso 1 1 calc R
C6 C 0.41822(10) 0.59752(12) 0.55818(6) 0.0238(3) Uani 1 1 d .
C8 C 0.76275(10) 0.78854(11) 0.66435(5) 0.0186(2) Uani 1 1 d .
C9 C 0.86791(10) 0.74368(11) 0.70962(6) 0.0211(2) Uani 1 1 d .
C10 C 0.95964(11) 0.66643(13) 0.66652(7) 0.0284(3) Uani 1 1 d .
H10A H 0.9899 0.7230 0.6302 0.043 Uiso 1 1 calc R
H10B H 0.9197 0.5889 0.6471 0.043 Uiso 1 1 calc R
H10C H 1.0277 0.6381 0.6948 0.043 Uiso 1 1 calc R
C11 C 0.93026(12) 0.86505(12) 0.73935(7) 0.0310(3) Uani 1 1 d .
H11A H 0.9609 0.9207 0.7028 0.047 Uiso 1 1 calc R
H11B H 0.9981 0.8372 0.7679 0.047 Uiso 1 1 calc R
H11C H 0.8718 0.9150 0.7664 0.047 Uiso 1 1 calc R
C12 C 0.82044(12) 0.65610(13) 0.76669(6) 0.0301(3) Uani 1 1 d .
H12A H 0.7806 0.5783 0.7475 0.045 Uiso 1 1 calc R
H12B H 0.7620 0.7058 0.7939 0.045 Uiso 1 1 calc R
H12C H 0.8884 0.6282 0.7951 0.045 Uiso 1 1 calc R
C13 C 0.34207(12) 0.47481(14) 0.56012(7) 0.0333(3) Uani 1 1 d .
H13A H 0.3946 0.3974 0.5555 0.050 Uiso 1 1 calc R
H13B H 0.2835 0.4766 0.5230 0.050 Uiso 1 1 calc R
H13C H 0.2985 0.4704 0.6031 0.050 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O8 0.0261(4) 0.0141(4) 0.0347(5) 0.0008(3) -0.0079(4) -0.0001(3)
N1 0.0200(5) 0.0201(5) 0.0203(4) -0.0025(4) -0.0003(4) -0.0019(4)
N7 0.0216(5) 0.0139(4) 0.0247(5) 0.0014(4) -0.0060(4) 0.0002(4)
C2 0.0185(5) 0.0185(5) 0.0169(5) -0.0025(4) -0.0004(4) 0.0009(4)
C3 0.0225(5) 0.0194(5) 0.0239(5) 0.0009(4) -0.0021(4) 0.0008(4)
C4 0.0283(6) 0.0265(6) 0.0294(6) 0.0034(5) -0.0071(5) 0.0058(5)
C5 0.0217(6) 0.0346(7) 0.0315(6) -0.0016(5) -0.0092(5) 0.0012(5)
C6 0.0198(5) 0.0270(6) 0.0246(6) -0.0053(5) -0.0008(4) -0.0020(4)
C8 0.0188(5) 0.0165(5) 0.0206(5) -0.0005(4) -0.0002(4) 0.0001(4)
C9 0.0205(5) 0.0179(5) 0.0248(5) 0.0008(4) -0.0054(4) -0.0010(4)
C10 0.0209(5) 0.0282(6) 0.0360(7) 0.0004(5) -0.0034(5) 0.0028(5)
C11 0.0314(6) 0.0230(6) 0.0386(7) -0.0010(5) -0.0157(5) -0.0027(5)
C12 0.0311(6) 0.0340(7) 0.0252(6) 0.0070(5) -0.0074(5) -0.0053(5)
C13 0.0265(6) 0.0343(7) 0.0390(7) -0.0027(6) -0.0051(5) -0.0091(5)
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
C2 N1 C6 118.28(10)
C8 N7 C2 126.89(9)
C8 N7 H7 120.8(9)
C2 N7 H7 112.0(9)
N1 C2 C3 123.59(10)
N1 C2 N7 112.78(9)
C3 C2 N7 123.62(10)
C4 C3 C2 117.09(11)
C4 C3 H3 121.5
C2 C3 H3 121.5
C5 C4 C3 120.25(11)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 118.69(11)
C4 C5 H5 120.7
C6 C5 H5 120.7
N1 C6 C5 122.10(11)
N1 C6 C13 116.13(11)
C5 C6 C13 121.76(11)
O8 C8 N7 121.99(10)
O8 C8 C9 122.40(10)
N7 C8 C9 115.61(9)
C11 C9 C12 109.59(10)
C11 C9 C8 109.03(9)
C12 C9 C8 110.34(9)
C11 C9 C10 109.29(10)
C12 C9 C10 109.85(10)
C8 C9 C10 108.72(9)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C6 C13 H13A 109.5
C6 C13 H13B 109.5
H13A C13 H13B 109.5
C6 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O8 C8 1.2241(14)
N1 C2 1.3370(14)
N1 C6 1.3452(14)
N7 C8 1.3689(14)
N7 C2 1.4104(14)
N7 H7 0.884(12)
C2 C3 1.3932(15)
C3 C4 1.3858(16)
C3 H3 0.9500
C4 C5 1.3808(18)
C4 H4 0.9500
C5 C6 1.3880(17)
C5 H5 0.9500
C6 C13 1.5020(17)
C8 C9 1.5351(15)
C9 C11 1.5288(16)
C9 C12 1.5320(16)
C9 C10 1.5387(17)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 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
N7 H7 O8 0.884(12) 2.128(13) 2.9928(12) 165.8(13) 7_755
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
C6 N1 C2 C3 -0.75(16)
C6 N1 C2 N7 -179.61(9)
C8 N7 C2 N1 -161.18(10)
C8 N7 C2 C3 19.96(17)
N1 C2 C3 C4 0.14(17)
N7 C2 C3 C4 178.88(10)
C2 C3 C4 C5 0.25(18)
C3 C4 C5 C6 -0.02(19)
C2 N1 C6 C5 1.00(16)
C2 N1 C6 C13 -177.87(10)
C4 C5 C6 N1 -0.63(19)
C4 C5 C6 C13 178.18(12)
C2 N7 C8 O8 -2.82(18)
C2 N7 C8 C9 177.20(10)
O8 C8 C9 C11 4.37(15)
N7 C8 C9 C11 -175.65(10)
O8 C8 C9 C12 124.77(12)
N7 C8 C9 C12 -55.24(13)
O8 C8 C9 C10 -114.69(12)
N7 C8 C9 C10 65.29(12)
_journal_paper_doi 10.1021/jp1063116