#------------------------------------------------------------------------------
#$Date: 2022-11-08 10:50:46 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279082 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106003.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_8106003
loop_
_publ_author_name
'Shi, Yun-Lian'
'Nie, Xu-Liang'
'Huang, Tao'
'Xie, Jin-Hui'
'Peng, Da-Yong'
'Shi, Xu-Gen'
'Li, Bao-Tong'
_publ_section_title
;
 Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine,
 C11H12N4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1271
_journal_page_last               1272
_journal_paper_doi               10.1515/ncrs-2019-0395
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C11 H12 N4'
_chemical_formula_sum            'C11 H12 N4'
_chemical_formula_weight         200.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                97.749(2)
_cell_angle_beta                 99.285(2)
_cell_angle_gamma                95.917(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6939(10)
_cell_length_b                   8.8034(13)
_cell_length_c                   9.1140(13)
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      3.02
_cell_volume                     520.90(13)
_computing_cell_refinement       'APEX2, SAINT and SADABS [1]'
_computing_data_collection       'APEX2, SAINT and SADABS [1]'
_computing_data_reduction        'APEX2, SAINT and SADABS [1]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3997
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         2.292
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       BKOCK
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.71(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0472P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1704
_reflns_number_total             1914
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0395_suppl.cif
_cod_data_source_block           3869_0m
_cod_database_code               8106003
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.05619(17) 0.25951(13) -0.03250(13) 0.0402(3) Uani 1 1 d . . . . .
C2 C -0.09646(18) 0.14156(14) -0.11425(14) 0.0452(3) Uani 1 1 d . . . . .
C3 C -0.0631(2) 0.07492(16) -0.25164(15) 0.0567(4) Uani 1 1 d . . . . .
H3 H -0.1600 -0.0021 -0.3101 0.068 Uiso 1 1 calc R U . . .
C4 C 0.1129(2) 0.12059(17) -0.30478(15) 0.0587(4) Uani 1 1 d . . . . .
H4 H 0.1359 0.0749 -0.3977 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2507(2) 0.23415(16) -0.21690(14) 0.0513(3) Uani 1 1 d . . . . .
H5 H 0.3689 0.2648 -0.2523 0.062 Uiso 1 1 calc R U . . .
C6 C -0.2837(2) 0.09282(18) -0.05320(18) 0.0609(4) Uani 1 1 d . . . . .
H6A H -0.3679 0.0111 -0.1235 0.091 Uiso 1 1 calc R U . . .
H6B H -0.3585 0.1792 -0.0379 0.091 Uiso 1 1 calc R U . . .
H6C H -0.2446 0.0569 0.0409 0.091 Uiso 1 1 calc R U . . .
C7 C 0.6646(2) 0.26637(18) 0.42313(16) 0.0623(4) Uani 1 1 d . . . . .
H7 H 0.7705 0.2221 0.4734 0.075 Uiso 1 1 calc R U . . .
C8 C 0.3451(2) 0.32414(16) 0.40451(15) 0.0531(3) Uani 1 1 d . . . . .
H8 H 0.2228 0.3239 0.4406 0.064 Uiso 1 1 calc R U . . .
C9 C 0.36044(18) 0.38898(13) 0.27669(13) 0.0414(3) Uani 1 1 d . . . . .
C10 C 0.5463(2) 0.38793(15) 0.23136(14) 0.0497(3) Uani 1 1 d . . . . .
H10 H 0.5652 0.4319 0.1466 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1842(2) 0.45392(15) 0.19308(14) 0.0499(3) Uani 1 1 d . . . . .
H11A H 0.1213 0.5156 0.2649 0.060 Uiso 1 1 calc R U . . .
H11B H 0.2353 0.5215 0.1281 0.060 Uiso 1 1 calc R U . . .
N1 N 0.22652(15) 0.30465(12) -0.08218(11) 0.0459(3) Uani 1 1 d . . . . .
N2 N 0.03137(15) 0.33502(13) 0.10314(12) 0.0509(3) Uani 1 1 d . . . . .
H2 H -0.0791 0.3110 0.1363 0.061 Uiso 1 1 calc R U . . .
N3 N 0.70141(17) 0.32686(15) 0.30310(14) 0.0610(4) Uani 1 1 d . . . . .
N4 N 0.4954(2) 0.26181(15) 0.47924(13) 0.0634(4) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 N2 116.77(11) . .
N1 C1 C2 123.27(11) . .
N2 C1 C2 119.96(11) . .
C3 C2 C1 116.36(12) . .
C3 C2 C6 122.14(12) . .
C1 C2 C6 121.51(12) . .
C2 C3 C4 121.04(12) . .
C5 C4 C3 117.94(12) . .
N1 C5 C4 123.93(12) . .
N4 C7 N3 127.43(13) . .
N4 C8 C9 123.71(12) . .
C10 C9 C8 115.06(12) . .
C10 C9 C11 123.06(11) . .
C8 C9 C11 121.88(11) . .
N3 C10 C9 123.22(12) . .
N2 C11 C9 112.69(10) . .
C1 N1 C5 117.46(11) . .
C1 N2 C11 122.36(10) . .
C7 N3 C10 115.33(12) . .
C7 N4 C8 115.24(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3359(15) .
C1 N2 1.3657(15) .
C1 C2 1.4158(17) .
C2 C3 1.3716(19) .
C2 C6 1.4975(18) .
C3 C4 1.387(2) .
C4 C5 1.359(2) .
C5 N1 1.3411(16) .
C7 N4 1.3150(19) .
C7 N3 1.3260(19) .
C8 N4 1.3304(18) .
C8 C9 1.3782(18) .
C9 C10 1.3733(18) .
C9 C11 1.5054(17) .
C10 N3 1.3361(17) .
C11 N2 1.4461(16) .
