#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/61/2236168.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_2236168
loop_
_publ_author_name
'Islor, Arun M.'
'Chandrakantha, B.'
'Shetty, Prakash'
'Gerber, Thomas'
'Hosten, Eric'
'Betz, Richard'
_publ_section_title
;
 Quinolin-3-amine
;
_journal_coeditor_code           CV5347
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3155
_journal_paper_doi               10.1107/S1600536812042626
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H8 N2'
_chemical_formula_moiety         'C9 H8 N2'
_chemical_formula_sum            'C9 H8 N2'
_chemical_formula_weight         144.17
_chemical_melting_point_gt       366
_chemical_melting_point_lt       368
_chemical_name_common
;
3-Aminoquinoline
;
_chemical_name_systematic
;
Quinolin-3-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                   7.6223(3)
_cell_length_b                   7.6289(3)
_cell_length_c                   12.6967(4)
_cell_measurement_reflns_used    5242
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.67
_cell_volume                     738.31(5)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6898
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0323
_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)+(0.0591P)²+0.1011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                1015
_reflns_number_total             1077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv5347.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               2236168
_cod_database_fobs_code          2236168
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
_atom_site_symmetry_multiplicity
N N1 0.25487(15) 0.26319(16) 0.38612(8) 0.0280(3) Uani d . 1 1
N N2 -0.18546(17) 0.08305(19) 0.39280(11) 0.0359(3) Uani d . 1 1
H H2A -0.258(3) 0.023(3) 0.3568(15) 0.056(6) Uiso d . 1 1
H H2B -0.198(2) 0.098(3) 0.4628(17) 0.043(5) Uiso d . 1 1
C C1 0.30327(17) 0.23241(17) 0.28353(9) 0.0249(3) Uani d . 1 1
C C2 0.09884(17) 0.21121(18) 0.41581(9) 0.0277(3) Uani d . 1 1
H H2 0.0663 0.2323 0.4869 0.033 Uiso calc R 1 1
C C3 -0.02593(17) 0.12565(16) 0.35016(9) 0.0253(3) Uani d . 1 1
C C4 0.02155(18) 0.09412(17) 0.24707(10) 0.0265(3) Uani d . 1 1
H H4 -0.0576 0.0376 0.2003 0.032 Uiso calc R 1 1
C C5 0.18933(16) 0.14693(17) 0.21189(9) 0.0244(3) Uani d . 1 1
C C6 0.24840(19) 0.11883(19) 0.10713(10) 0.0299(3) Uani d . 1 1
H H6 0.1743 0.0609 0.0580 0.036 Uiso calc R 1 1
C C7 0.4113(2) 0.17449(19) 0.07635(10) 0.0344(3) Uani d . 1 1
H H7 0.4488 0.1553 0.0059 0.041 Uiso calc R 1 1
C C8 0.52397(19) 0.2599(2) 0.14793(11) 0.0353(3) Uani d . 1 1
H H8 0.6366 0.2982 0.1256 0.042 Uiso calc R 1 1
C C9 0.47097(17) 0.28794(19) 0.25005(11) 0.0313(3) Uani d . 1 1
H H9 0.5474 0.3448 0.2982 0.038 Uiso calc R 1 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C1 117.72(11)
C3 N2 H2A 119.4(14)
C3 N2 H2B 116.8(12)
H2A N2 H2B 122.1(18)
N1 C1 C9 118.50(12)
N1 C1 C5 121.52(12)
C9 C1 C5 119.98(11)
N1 C2 C3 125.27(11)
N1 C2 H2 117.4
C3 C2 H2 117.4
N2 C3 C4 124.50(12)
N2 C3 C2 118.07(11)
C4 C3 C2 117.42(12)
C3 C4 C5 119.19(12)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C1 118.88(11)
C4 C5 C6 122.66(12)
C1 C5 C6 118.45(12)
C7 C6 C5 120.52(13)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C8 120.78(12)
C6 C7 H7 119.6
C8 C7 H7 119.6
C9 C8 C7 120.04(13)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C1 120.22(13)
C8 C9 H9 119.9
C1 C9 H9 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3091(17)
N1 C1 1.3740(16)
N2 C3 1.3701(17)
N2 H2A 0.85(2)
N2 H2B 0.90(2)
C1 C9 1.4122(18)
C1 C5 1.4167(17)
C2 C3 1.4231(17)
C2 H2 0.9500
C3 C4 1.3792(17)
C4 C5 1.4133(18)
C4 H4 0.9500
C5 C6 1.4205(17)
C6 C7 1.369(2)
C6 H6 0.9500
C7 C8 1.410(2)
C7 H7 0.9500
C8 C9 1.375(2)
C8 H8 0.9500
C9 H9 0.9500
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
N2 H2B N1 3_456 0.90(2) 2.22(2) 3.0761(17) 158.2(18)
N2 H2A Cg 4_545 0.85(2) 2.60(2) 3.3101(15) 142.3(19)
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
C2 N1 C1 C9 179.86(12)
C2 N1 C1 C5 -0.20(19)
C1 N1 C2 C3 -0.3(2)
N1 C2 C3 N2 -178.55(13)
N1 C2 C3 C4 0.3(2)
N2 C3 C4 C5 178.95(12)
C2 C3 C4 C5 0.15(18)
C3 C4 C5 C1 -0.61(18)
C3 C4 C5 C6 179.80(12)
N1 C1 C5 C4 0.66(18)
C9 C1 C5 C4 -179.41(11)
N1 C1 C5 C6 -179.74(12)
C9 C1 C5 C6 0.20(18)
C4 C5 C6 C7 179.12(12)
C1 C5 C6 C7 -0.5(2)
C5 C6 C7 C8 0.3(2)
C6 C7 C8 C9 0.1(2)
C7 C8 C9 C1 -0.4(2)
N1 C1 C9 C8 -179.82(13)
C5 C1 C9 C8 0.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10897
