#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/68/2236849.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_2236849
loop_
_publ_author_name
'Draguta, Sergiu'
'Khrustalev, Victor N.'
'Sandhu, Bhupinder'
'Antipin, Mikhail Yu.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 6-Methylpyridin-2-amine
;
_journal_coeditor_code           CV5366
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3466
_journal_paper_doi               10.1107/S1600536812047800
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H8 N2'
_chemical_formula_moiety         'C6 H8 N2'
_chemical_formula_sum            'C6 H8 N2'
_chemical_formula_weight         108.14
_chemical_name_systematic
;
6-Methylpyridin-2-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.952(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1006(11)
_cell_length_b                   6.2458(8)
_cell_length_c                   10.5598(13)
_cell_measurement_reflns_used    2436
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.28
_cell_volume                     589.29(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5852
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0431
_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)+(0.082P)²+0.126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                1196
_reflns_number_total             1420
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5366.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236849
_cod_database_fobs_code          2236849
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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 0.17331(10) 0.50475(14) 0.92049(8) 0.0227(3) Uani d . 1 1
N N2 -0.00315(12) 0.77129(17) 0.90952(10) 0.0311(3) Uani d . 1 1
H H2A -0.0502(18) 0.693(3) 0.9607(16) 0.040(4) Uiso d . 1 1
H H2B -0.0533(18) 0.877(3) 0.8697(15) 0.038(4) Uiso d . 1 1
C C2 0.11252(12) 0.68485(17) 0.86263(10) 0.0234(3) Uani d . 1 1
C C3 0.16561(13) 0.77898(18) 0.75860(11) 0.0271(3) Uani d . 1 1
H H3 0.1219 0.9029 0.7196 0.033 Uiso calc R 1 1
C C4 0.28303(13) 0.68378(19) 0.71621(10) 0.0281(3) Uani d . 1 1
H H4 0.3191 0.7419 0.6470 0.034 Uiso calc R 1 1
C C5 0.34831(12) 0.49983(18) 0.77700(10) 0.0267(3) Uani d . 1 1
H H5 0.4291 0.4349 0.7500 0.032 Uiso calc R 1 1
C C6 0.29036(12) 0.41577(17) 0.87838(10) 0.0234(3) Uani d . 1 1
C C7 0.35535(13) 0.21888(19) 0.94938(11) 0.0307(3) Uani d . 1 1
H H7A 0.4172 0.2597 1.0298 0.046 Uiso calc R 1 1
H H7B 0.4146 0.1429 0.8980 0.046 Uiso calc R 1 1
H H7C 0.2758 0.1282 0.9656 0.046 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 C6 118.43(9)
C2 N2 H2A 119.7(10)
C2 N2 H2B 120.1(10)
H2A N2 H2B 116.2(14)
N1 C2 N2 116.52(10)
N1 C2 C3 121.96(10)
N2 C2 C3 121.51(10)
C4 C3 C2 118.53(10)
C4 C3 H3 120.7
C2 C3 H3 120.7
C3 C4 C5 119.88(10)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 118.53(10)
C6 C5 H5 120.7
C4 C5 H5 120.7
N1 C6 C5 122.65(10)
N1 C6 C7 115.68(9)
C5 C6 C7 121.67(10)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3476(14)
N1 C6 1.3496(13)
N2 C2 1.3575(14)
N2 H2A 0.896(17)
N2 H2B 0.867(17)
C2 C3 1.4099(15)
C3 C4 1.3702(16)
C3 H3 0.9300
C4 C5 1.3929(16)
C4 H4 0.9300
C5 C6 1.3837(15)
C5 H5 0.9300
C6 C7 1.5019(15)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
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
N2 H2A N1 3_567 0.896(17) 2.211(17) 3.1062(14) 177.5(11) yes
N2 H2B Cg 2_554 0.867(17) 2.674(16) 3.4875(12) 163.5(11) yes
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 N2 -178.81(9)
C6 N1 C2 C3 1.34(15)
N1 C2 C3 C4 -0.31(17)
N2 C2 C3 C4 179.84(10)
C2 C3 C4 C5 -0.88(17)
C3 C4 C5 C6 1.01(17)
C2 N1 C6 C5 -1.20(16)
C2 N1 C6 C7 178.40(9)
C4 C5 C6 N1 0.04(17)
C4 C5 C6 C7 -179.54(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14991
