#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/58/2015896.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015896
loop_
_publ_author_name
'Montaño, Ángela Marcela'
'Henao, José  Antonio'
'Vargas-Méndez, Leonor Y.'
'Kouznetsov, Vladimir V.'
'Atencio, Reinaldo'
_publ_section_title
;
 4,6-Dimethyl-2-(3-pyridyl)quinolin-5-amine
;
_journal_coeditor_code           GD3088
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o228
_journal_page_last               o230
_journal_paper_doi               10.1107/S0108270107006221
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H15 N3'
_chemical_formula_moiety         'C16 H15 N3'
_chemical_formula_sum            'C16 H15 N3'
_chemical_formula_weight         249.31
_chemical_name_systematic
;
4,6-Dimethyl-2-(3-pyridyl)quinolin-5-amine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   9.397(3)
_cell_length_b                   18.314(2)
_cell_length_c                   7.399(4)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      20
_cell_volume                     1273.3(8)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1993)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 1999)
;
_computing_molecular_graphics    'MaterialStudio (Accelrys, 2002)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    'SHELXTL-Plus (Bruker, 1999)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1447
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.9485
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL-Plus
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0379
_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)+(0.0607P)²+0.1555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                1138
_reflns_number_total             1309
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3088.cif
_cod_data_source_block           I
_cod_original_cell_volume        1273.4(8)
_cod_database_code               2015896
_cod_database_fobs_code          2015896
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'
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_refinement_flags
_atom_site_occupancy
N N1 0.9153(2) 0.42667(11) -0.0123(3) 0.0399(5) Uani d . 1
N N2 1.1038(3) 0.67413(12) -0.1028(4) 0.0644(8) Uani d . 1
H H2A 1.1761 0.7027 -0.0942 0.077 Uiso calc R 1
H H2B 1.0274 0.6890 -0.1552 0.077 Uiso calc R 1
N N3 0.6600(3) 0.25546(12) -0.1636(4) 0.0592(7) Uani d . 1
C C1 0.7888(3) 0.44510(13) -0.0762(3) 0.0398(6) Uani d . 1
C C2 0.7521(3) 0.51823(13) -0.1114(4) 0.0435(6) Uani d . 1
H H2C 0.6597 0.5293 -0.1470 0.052 Uiso calc R 1
C C3 0.8495(3) 0.57342(13) -0.0944(3) 0.0419(6) Uani d . 1
C C4 0.9910(3) 0.55483(13) -0.0414(3) 0.0374(6) Uani d . 1
C C5 1.1104(3) 0.60344(13) -0.0317(4) 0.0436(6) Uani d . 1
C C6 1.2355(3) 0.58178(14) 0.0514(4) 0.0459(7) Uani d . 1
C C7 1.2492(3) 0.50951(15) 0.1124(4) 0.0489(7) Uani d . 1
H H7 1.3323 0.4955 0.1711 0.059 Uiso calc R 1
C C8 1.1442(3) 0.45955(13) 0.0880(4) 0.0452(7) Uani d . 1
H H8 1.1585 0.4114 0.1232 0.054 Uiso calc R 1
C C9 1.0140(3) 0.48030(13) 0.0097(3) 0.0380(6) Uani d . 1
C C11 1.3600(3) 0.63368(16) 0.0729(5) 0.0677(9) Uani d . 1
H H11B 1.3301 0.6757 0.1405 0.102 Uiso d R 1
H H11C 1.3915 0.6499 -0.0439 0.102 Uiso d R 1
H H11A 1.4386 0.6117 0.1354 0.102 Uiso d R 1
C C10 0.7974(3) 0.65075(13) -0.1239(4) 0.0534(7) Uani d . 1
H H10A 0.8021 0.6635 -0.2496 0.080 Uiso d R 1
H H10B 0.8561 0.6842 -0.0573 0.080 Uiso d R 1
H H10C 0.7009 0.6536 -0.0819 0.080 Uiso d R 1
C C12 0.6869(3) 0.38412(13) -0.1032(3) 0.0410(6) Uani d . 1
C C13 0.7389(3) 0.31504(14) -0.1437(4) 0.0477(7) Uani d . 1
H H13 0.8368 0.3101 -0.1580 0.057 Uiso calc R 1
C C14 0.5195(3) 0.26343(17) -0.1370(5) 0.0599(8) Uani d . 1
H H14 0.4619 0.2222 -0.1443 0.072 Uiso calc R 1
C C15 0.4568(3) 0.32930(17) -0.0997(5) 0.0574(8) Uani d . 1
H H15 0.3587 0.3326 -0.0851 0.069 Uiso calc R 1
C C16 0.5405(3) 0.39026(16) -0.0842(4) 0.0530(7) Uani d . 1
H H16 0.4994 0.4355 -0.0610 0.064 Uiso calc R 1
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C9 118.1(2) ?
C5 N2 H2A 120.0 ?
C5 N2 H2B 120.0 ?
H2A N2 H2B 120.0 ?
C13 N3 C14 116.3(3) ?
N1 C1 C2 121.9(2) ?
N1 C1 C12 115.8(2) ?
C2 C1 C12 122.2(2) ?
C3 C2 C1 121.4(2) ?
C3 C2 H2C 119.3 ?
C1 C2 H2C 119.3 ?
C2 C3 C4 118.2(2) y
C2 C3 C10 117.4(2) y
C4 C3 C10 124.3(2) y
C3 C4 C9 116.1(2) y
C3 C4 C5 126.5(2) y
C9 C4 C5 117.4(2) y
C6 C5 N2 118.0(2) y
C6 C5 C4 120.6(2) y
N2 C5 C4 121.4(2) y
C5 C6 C7 119.3(2) ?
C5 C6 C11 121.5(2) ?
C7 C6 C11 119.1(2) ?
C8 C7 C6 121.8(3) ?
C8 C7 H7 119.1 ?
C6 C7 H7 119.1 ?
C7 C8 C9 120.3(2) ?
C7 C8 H8 119.8 ?
C9 C8 H8 119.8 ?
N1 C9 C8 116.6(2) ?
N1 C9 C4 123.6(2) ?
C8 C9 C4 119.8(2) ?
C6 C11 H11B 109.4 ?
C6 C11 H11C 109.7 ?
H11B C11 H11C 108.2 ?
C6 C11 H11A 112.4 ?
H11B C11 H11A 108.1 ?
H11C C11 H11A 109.1 ?
C3 C10 H10A 110.6 ?
C3 C10 H10B 109.7 ?
H10A C10 H10B 108.4 ?
C3 C10 H10C 108.0 ?
H10A C10 H10C 110.1 ?
H10B C10 H10C 110.1 ?
C16 C12 C13 116.4(3) ?
C16 C12 C1 124.4(2) ?
C13 C12 C1 119.2(2) ?
N3 C13 C12 125.2(3) ?
N3 C13 H13 117.4 ?
C12 C13 H13 117.4 ?
N3 C14 C15 123.2(3) ?
N3 C14 H14 118.4 ?
C15 C14 H14 118.4 ?
C14 C15 C16 119.1(3) ?
C14 C15 H15 120.4 ?
C16 C15 H15 120.4 ?
C15 C16 C12 119.6(3) ?
C15 C16 H16 120.2 ?
C12 C16 H16 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.323(3) y
C1 C2 1.407(3) y
C2 C3 1.369(4) y
C3 C4 1.427(4) y
C4 C5 1.434(4) y
C5 C6 1.385(4) y
C6 C7 1.404(4) y
C7 C8 1.357(4) y
C8 C9 1.406(3) y
C9 N1 1.361(3) y
C4 C9 1.433(3) y
C1 C12 1.485(3) y
C3 C10 1.514(3) y
C5 N2 1.399(3) y
N2 H2A 0.8600 ?
N2 H2B 0.8600 ?
N3 C13 1.327(3) ?
N3 C14 1.343(4) ?
C2 H2C 0.9300 ?
C6 C11 1.516(4) ?
C7 H7 0.9300 ?
C8 H8 0.9300 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C11 H11A 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C12 C16 1.387(4) ?
C12 C13 1.389(3) ?
C13 H13 0.9300 ?
C14 C15 1.371(4) ?
C14 H14 0.9300 ?
C15 C16 1.371(4) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C10 H10B N2 1_555 0.96 2.36 2.915(4) 116 yes
N2 H2A N3 4_754 0.86 2.55 3.183(4) 131 yes
C7 H7 CgA 2_765 0.93 2.74 3.405(4) 129 yes
C10 H10A CgB 2_664 0.96 2.91 3.838(4) 162 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8642655
