#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228316.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_2228316
loop_
_publ_author_name
'Jayaratna, Naleen B.'
'Norman, Richard E.'
_publ_section_title
;
 2-Phenyl-2-(pyridin-2-yl)hexahydropyrimidine
;
_journal_coeditor_code           FL2327
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3149
_journal_paper_doi               10.1107/S1600536810045976
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H17 N3'
_chemical_formula_moiety         'C15 H17 N3'
_chemical_formula_sum            'C15 H17 N3'
_chemical_formula_weight         239.32
_chemical_name_systematic
;
2-Phenyl-2-(pyridin-2-yl)-hexahydropyrimidine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                97.2770(10)
_cell_angle_beta                 94.2160(10)
_cell_angle_gamma                112.0360(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2173(2)
_cell_length_b                   9.0211(2)
_cell_length_c                   9.1481(3)
_cell_measurement_reflns_used    5072
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      68.4
_cell_measurement_theta_min      4.9
_cell_volume                     618.11(3)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'TEXSAN for Windows (Molecular Structure Corporation, 1999)'
_computing_structure_refinement
'TEXSAN for Windows (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.02240
_diffrn_reflns_av_sigmaI/netI    0.044
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6458
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         4.91
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       fragment
_exptl_crystal_F_000             256.00
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       0.000012(5)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p. 213'
_refine_ls_extinction_method     'Zachariasen (1968)'
_refine_ls_goodness_of_fit_all   1.025
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.0100
_refine_ls_shift/su_mean         0.0018
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00563|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.1660
_refine_ls_wR_factor_ref         0.1660
_reflns_number_gt                2159
_reflns_number_total             2159
_reflns_threshold_expression     I>10σ(I)
_cod_data_source_file            fl2327.cif
_cod_data_source_block           I
_cod_database_code               2228316
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,   -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.25511(12) 0.17532(11) 0.94163(10) 0.0178(2) Uani d 1 . .
N N2 0.30025(12) 0.06793(11) 0.55486(10) 0.0164(3) Uani d 1 . .
N N3 0.51826(11) 0.16009(11) 0.77508(11) 0.0160(2) Uani d 1 . .
C C1 0.1439(2) 0.21730(10) 1.02090(13) 0.0193(3) Uani d 1 . .
C C2 -0.02230(10) 0.20332(13) 0.96108(13) 0.0190(3) Uani d 1 . .
C C3 -0.07658(13) 0.14186(13) 0.81117(13) 0.0186(3) Uani d 1 . .
C C4 0.03660(10) 0.09780(13) 0.72750(12) 0.0167(3) Uani d 1 . .
C C5 0.20160(10) 0.11659(12) 0.79702(12) 0.0147(3) Uani d 1 . .
C C6 0.33262(13) 0.06232(13) 0.71334(12) 0.0150(3) Uani d 1 . .
C C7 0.28971(13) -0.11566(13) 0.72936(12) 0.0145(3) Uani d 1 . .
C C8 0.12460(10) -0.23417(13) 0.66514(12) 0.0175(3) Uani d 1 . .
C C9 0.07920(10) -0.39534(13) 0.68074(12) 0.0193(3) Uani d 1 . .
C C10 0.1985(2) -0.44127(13) 0.76044(13) 0.0205(3) Uani d 1 . .
C C11 0.36250(10) -0.32470(10) 0.82420(12) 0.0197(3) Uani d 1 . .
C C12 0.40780(10) -0.16293(13) 0.80897(12) 0.0173(3) Uani d 1 . .
C C13 0.3650(2) 0.23390(10) 0.52058(12) 0.0187(3) Uani d 1 . .
C C14 0.55600(10) 0.33528(13) 0.58810(13) 0.0207(3) Uani d 1 . .
C C15 0.57550(10) 0.32995(13) 0.75312(13) 0.0185(3) Uani d 1 . .
H H1 0.1808 0.2589 1.1238 0.023 Uiso c 1 . .
H H2 -0.0969 0.2351 1.0213 0.023 Uiso c 1 . .
H H3 -0.1898 0.1301 0.7665 0.022 Uiso c 1 . .
H H4 0.0025 0.0555 0.6245 0.020 Uiso c 1 . .
H H5 0.0428 -0.2038 0.6103 0.021 Uiso c 1 . .
H H6 -0.0333 -0.4744 0.6370 0.023 Uiso c 1 . .
H H7 0.1679 -0.5515 0.7711 0.025 Uiso c 1 . .
H H8 0.4444 -0.3555 0.8786 0.024 Uiso c 1 . .
H H9 0.5202 -0.0841 0.8533 0.021 Uiso c 1 . .
H H10 0.3572 0.2277 0.4157 0.023 Uiso c 1 . .
H H11 0.2919 0.2860 0.5582 0.023 Uiso c 1 . .
H H12 0.6325 0.2926 0.5417 0.025 Uiso c 1 . .
H H13 0.5862 0.4443 0.5733 0.025 Uiso c 1 . .
H H14 0.5040 0.3781 0.8004 0.022 Uiso c 1 . .
H H15 0.6958 0.3878 0.7947 0.022 Uiso c 1 . .
H H16 0.521(2) 0.160(2) 0.874(2) 0.016 Uiso d 1 . .
H H17 0.350(2) 0.008(2) 0.503(2) 0.016 Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N 0.0311 0.0180
;International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C 0.0181 0.0091
;International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H 0.000 0.000
;International Tables for Crystallography
(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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 117.65(9) n
H17 N2 C6 . . 108.9(8) n
H17 N2 C13 . . 110.7(8) n
C6 N2 C13 . . 113.36(8) n
H16 N3 C6 . . 104.7(8) n
H16 N3 C15 . . 107.2(8) n
C6 N3 C15 . . 112.82(9) n
H1 C1 N1 . . 118.2 n
H1 C1 C2 . . 118.2 n
N1 C1 C2 . . 123.62(10) n
H2 C2 C3 . . 120.9 n
H2 C2 C1 . . 120.9 n
C3 C2 C1 . . 118.23(10) n
H3 C3 C4 . . 120.5 n
H3 C3 C2 . . 120.5 n
C4 C3 C2 . . 118.97(10) n
H4 C4 C3 . . 120.6 n
H4 C4 C5 . . 120.6 n
C3 C4 C5 . . 118.85(10) n
N1 C5 C4 . . 122.68(10) n
N1 C5 C6 . . 115.06(9) n
C4 C5 C6 . . 122.19(9) n
N2 C6 N3 . . 111.48(9) n
N2 C6 C7 . . 107.67(8) n
N2 C6 C5 . . 109.10(8) n
N3 C6 C7 . . 109.07(9) n
N3 C6 C5 . . 112.26(8) n
C7 C6 C5 . . 107.06(8) n
C12 C7 C8 . . 118.61(10) n
C12 C7 C6 . . 122.22(10) n
C8 C7 C6 . . 119.15(10) n
H5 C8 C9 . . 119.6 n
H5 C8 C7 . . 119.6 n
C9 C8 C7 . . 120.82(10) n
H6 C9 C8 . . 120.0 n
H6 C9 C10 . . 120.0 n
C8 C9 C10 . . 120.06(10) n
H7 C10 C11 . . 120.2 n
H7 C10 C9 . . 120.2 n
C11 C10 C9 . . 119.50(10) n
H8 C11 C10 . . 119.8 n
H8 C11 C12 . . 119.8 n
C10 C11 C12 . . 120.40(10) n
H9 C12 C7 . . 119.7 n
H9 C12 C11 . . 119.7 n
C7 C12 C11 . . 120.60(10) n
H10 C13 H11 . . 109.5 n
H10 C13 N2 . . 108.6 n
H10 C13 C14 . . 108.6 n
H11 C13 N2 . . 108.6 n
H11 C13 C14 . . 108.6 n
N2 C13 C14 . . 113.03(9) n
H13 C14 H12 . . 109.5 n
H13 C14 C15 . . 109.5 n
H13 C14 C13 . . 109.5 n
H12 C14 C15 . . 109.5 n
H12 C14 C13 . . 109.5 n
C15 C14 C13 . . 109.24(9) n
H15 C15 H14 . . 109.5 n
H15 C15 N3 . . 109.6 n
H15 C15 C14 . . 109.6 n
H14 C15 N3 . . 109.6 n
H14 C15 C14 . . 109.6 n
N3 C15 C14 . . 109.21(9) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.339(2) n
N1 C5 . 1.337(2) n
N2 H17 . 0.910(10) n
N2 C6 . 1.4650(10) n
N2 C13 . 1.4730(13) n
N3 H16 . 0.900(10) n
N3 C6 . 1.4702(12) n
N3 C15 . 1.4699(13) n
C1 H1 . 0.95 n
C1 C2 . 1.387(2) n
C2 H2 . 0.95 n
C2 C3 . 1.385(2) n
C3 H3 . 0.95 n
C3 C4 . 1.383(2) n
C4 H4 . 0.95 n
C4 C5 . 1.395(2) n
C5 C6 . 1.5510(10) n
C6 C7 . 1.5380(10) n
C7 C12 . 1.392(2) n
C7 C8 . 1.4010(10) n
C8 H5 . 0.95 n
C8 C9 . 1.388(2) n
C9 H6 . 0.95 n
C9 C10 . 1.393(2) n
C10 H7 . 0.95 n
C10 C11 . 1.388(2) n
C11 H8 . 0.95 n
C11 C12 . 1.393(2) n
C12 H9 . 0.95 n
C13 H10 . 0.95 n
C13 H11 . 0.95 n
C13 C14 . 1.5230(10) n
C14 H13 . 0.95 n
C14 H12 . 0.95 n
C14 C15 . 1.515(2) n
C15 H15 . 0.95 n
C15 H14 . 0.95 n
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N1 C11 3.3730(10) . 2_657 n
N1 C2 3.498(2) . 2_557 n
N1 C12 3.501(2) . 2_657 n
N2 C4 3.381(2) . 2_556 n
N3 C3 3.3890(10) . 1_655 n
C1 C2 3.572(2) . 2_557 n
C2 C8 3.582(2) . 2_557 n
C9 C9 3.484(2) . 2_546 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H16 N1 . . . 0.900(10) 2.365(13) 2.7696(12) 107.1(10)
N2 H17 N3 . . 2_656 0.910(10) 3.250(10) 4.1179(13) 160.2(10)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.3(2) n
N1 C5 C4 C3 . . . . 0.1(2) n
N1 C5 C6 N2 . . . . -155.92(9) n
N1 C5 C6 N3 . . . . -31.80(10) n
N1 C5 C6 C7 . . . . 87.80(10) n
N2 C6 N3 C15 . . . . 56.40(10) n
N2 C6 C5 C4 . . . . 27.10(10) n
N2 C6 C7 C8 . . . . -52.80(10) n
N2 C6 C7 C12 . . . . 128.90(10) n
N2 C13 C14 C15 . . . . -52.80(10) n
N3 C6 N2 C13 . . . . -50.50(10) n
N3 C6 C5 C4 . . . . 151.20(10) n
N3 C6 C7 C8 . . . . -173.95(9) n
N3 C6 C7 C12 . . . . 7.70(10) n
N3 C15 C14 C13 . . . . 56.70(10) n
C1 N1 C5 C4 . . . . -0.1(2) n
C1 N1 C5 C6 . . . . -177.08(9) n
C1 C2 C3 C4 . . . . -0.3(2) n
C2 C1 N1 C5 . . . . -0.1(2) n
C2 C3 C4 C5 . . . . 0.1(2) n
C3 C4 C5 C6 . . . . 176.89(9) n
C4 C5 C6 C7 . . . . -89.20(10) n
C5 C6 N2 C13 . . . . 74.10(10) n
C5 C6 N3 C15 . . . . -66.40(10) n
C5 C6 C7 C8 . . . . 64.40(10) n
C5 C6 C7 C12 . . . . -114.00(10) n
C6 N2 C13 C14 . . . . 50.10(10) n
C6 N3 C15 C14 . . . . -60.00(10) n
C6 C7 C8 C9 . . . . -178.20(8) n
C6 C7 C12 C11 . . . . 178.39(9) n
C7 C6 N2 C13 . . . . -170.05(8) n
C7 C6 N3 C15 . . . . 175.14(8) n
C7 C8 C9 C10 . . . . -0.3(2) n
C7 C12 C11 C10 . . . . -0.2(2) n
C8 C7 C12 C11 . . . . 0.1(2) n
C8 C9 C10 C11 . . . . 0.2(2) n
C9 C8 C7 C12 . . . . 0.2(2) n
C9 C10 C11 C12 . . . . 0.1(2) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656349
