#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222431.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_2222431
loop_
_publ_author_name
'Tang, Shi-Gui'
'Yang, Cheng-Long'
'Chen, Jun-Hua'
'Bi, Sheng'
'Guo, Cheng'
_publ_section_title
;
 4-Methyl-3-[4-(3-pyridyl)pyrimidin-2-yloxy]aniline
;
_journal_coeditor_code           PV2165
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1707
_journal_paper_doi               10.1107/S1600536809023770
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H14 N4 O'
_chemical_formula_moiety         'C16 H14 N4 O'
_chemical_formula_sum            'C16 H14 N4 O'
_chemical_formula_weight         278.31
_chemical_name_systematic
;
4-Methyl-3-[4-(3-pyridyl)pyrimidin-2-yloxy]aniline
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5800(17)
_cell_length_b                   20.360(4)
_cell_length_c                   8.0780(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1396.4(5)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2698
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.300
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0609
_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)+(0.06P)²+1.4P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                1587
_reflns_number_total             2526
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2165.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222431
_cod_database_fobs_code          2222431
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_disorder_assembly
_atom_site_disorder_group
O O 0.1194(2) 0.51325(11) 0.7760(3) 0.0508(6) Uani d . 1 . .
N N1 -0.2002(3) 0.66654(13) 1.0241(4) 0.0543(8) Uani d . 1 . .
H H1A -0.2537 0.7024 1.0186 0.065 Uiso calc R 1 . .
H H1B -0.1955 0.6419 1.1111 0.065 Uiso calc R 1 . .
C C1 0.1120(5) 0.5926(2) 0.4732(5) 0.0680(11) Uani d . 1 . .
H H1C 0.1658 0.5515 0.4963 0.102 Uiso calc R 1 . .
H H1D 0.1862 0.6258 0.4525 0.102 Uiso calc R 1 . .
H H1E 0.0335 0.5879 0.3765 0.102 Uiso calc R 1 . .
N N2 0.3246(3) 0.44734(12) 0.7623(3) 0.0416(7) Uani d . 1 . .
C C2 0.0341(4) 0.61219(17) 0.6213(4) 0.0460(8) Uani d . 1 . .
N N3 0.3632(3) 0.56324(13) 0.7919(4) 0.0497(7) Uani d . 1 . .
C C3 -0.0526(4) 0.66983(17) 0.6214(4) 0.0498(9) Uani d . 1 . .
H H3B -0.0593 0.6973 0.5285 0.060 Uiso calc R 1 . .
C C4 -0.1290(4) 0.68813(16) 0.7523(4) 0.0480(9) Uani d . 1 . .
H H4A -0.1857 0.7272 0.7468 0.058 Uiso calc R 1 . .
N N4 0.4792(4) 0.26228(15) 0.6373(4) 0.0649(9) Uani d . 1 . .
C C5 -0.1216(3) 0.64847(14) 0.8928(4) 0.0405(8) Uani d . 1 . .
C C6 -0.0318(3) 0.59152(14) 0.8984(4) 0.0395(8) Uani d . 1 . .
H H6A -0.0230 0.5645 0.9921 0.047 Uiso calc R 1 . .
C C7 0.0441(3) 0.57516(15) 0.7653(4) 0.0403(8) Uani d . 1 . .
C C8 0.2772(4) 0.50942(15) 0.7753(4) 0.0412(8) Uani d . 1 . .
C C9 0.4799(4) 0.43896(15) 0.7646(4) 0.0406(8) Uani d . 1 . .
C C10 0.5823(4) 0.49200(17) 0.7776(5) 0.0522(9) Uani d . 1 . .
H H10A 0.6898 0.4863 0.7773 0.063 Uiso calc R 1 . .
C C11 0.5179(4) 0.55349(17) 0.7909(5) 0.0556(10) Uani d . 1 . .
H H11A 0.5845 0.5898 0.7995 0.067 Uiso calc R 1 . .
C C12 0.5341(4) 0.37050(15) 0.7517(4) 0.0411(8) Uani d . 1 . .
C C13 0.4408(4) 0.32551(17) 0.6553(5) 0.0526(9) Uani d . 1 . .
H H13A 0.3447 0.3400 0.5990 0.063 Uiso calc R 1 . .
C C14 0.6177(5) 0.24293(19) 0.7200(5) 0.0630(11) Uani d . 1 . .
H H14A 0.6476 0.1993 0.7104 0.076 Uiso calc R 1 . .
C C15 0.7182(5) 0.28438(19) 0.8184(5) 0.0619(10) Uani d . 1 . .
H H15A 0.8136 0.2687 0.8737 0.074 Uiso calc R 1 . .
C C16 0.6774(4) 0.34860(18) 0.8347(5) 0.0531(9) Uani d . 1 . .
H H16A 0.7445 0.3772 0.9004 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'
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O C7 . . 119.9(2) ?
C5 N1 H1A . . 120.0 ?
C5 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C2 C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C2 C1 H1E . . 109.5 ?
H1C C1 H1E . . 109.5 ?
H1D C1 H1E . . 109.5 ?
C8 N2 C9 . . 115.6(3) ?
C7 C2 C3 . . 115.5(3) ?
C7 C2 C1 . . 123.0(3) ?
C3 C2 C1 . . 121.5(3) ?
C8 N3 C11 . . 114.6(3) ?
C4 C3 C2 . . 123.0(3) ?
C4 C3 H3B . . 118.5 ?
C2 C3 H3B . . 118.5 ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C14 N4 C13 . . 116.3(3) ?
C4 C5 N1 . . 120.1(3) ?
C4 C5 C6 . . 118.2(3) ?
N1 C5 C6 . . 121.7(3) ?
C7 C6 C5 . . 119.9(3) ?
C7 C6 H6A . . 120.0 ?
C5 C6 H6A . . 120.0 ?
C6 C7 C2 . . 123.2(3) ?
C6 C7 O . . 115.6(3) ?
C2 C7 O . . 120.8(3) ?
N3 C8 N2 . . 128.5(3) ?
N3 C8 O . . 119.8(3) ?
N2 C8 O . . 111.7(3) ?
N2 C9 C10 . . 121.3(3) ?
N2 C9 C12 . . 116.2(3) ?
C10 C9 C12 . . 122.5(3) ?
C11 C10 C9 . . 117.1(3) ?
C11 C10 H10A . . 121.4 ?
C9 C10 H10A . . 121.4 ?
N3 C11 C10 . . 122.8(3) ?
N3 C11 H11A . . 118.6 ?
C10 C11 H11A . . 118.6 ?
C13 C12 C16 . . 117.5(3) ?
C13 C12 C9 . . 120.1(3) ?
C16 C12 C9 . . 122.4(3) ?
N4 C13 C12 . . 124.5(3) ?
N4 C13 H13A . . 117.8 ?
C12 C13 H13A . . 117.8 ?
N4 C14 C15 . . 123.1(3) ?
N4 C14 H14A . . 118.4 ?
C15 C14 H14A . . 118.4 ?
C16 C15 C14 . . 119.7(4) ?
C16 C15 H15A . . 120.2 ?
C14 C15 H15A . . 120.2 ?
C15 C16 C12 . . 118.9(4) ?
C15 C16 H16A . . 120.5 ?
C12 C16 H16A . . 120.5 ?
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
O C8 . 1.357(4) ?
O C7 . 1.413(4) ?
N1 C5 . 1.387(4) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
C1 C2 . 1.506(5) ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C1 H1E . 0.9600 ?
N2 C8 . 1.337(4) ?
N2 C9 . 1.340(4) ?
C2 C7 . 1.379(5) ?
C2 C3 . 1.389(5) ?
N3 C8 . 1.317(4) ?
N3 C11 . 1.344(4) ?
C3 C4 . 1.374(5) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.387(4) ?
C4 H4A . 0.9300 ?
N4 C14 . 1.336(5) ?
N4 C13 . 1.342(4) ?
C5 C6 . 1.389(4) ?
C6 C7 . 1.376(4) ?
C6 H6A . 0.9300 ?
C9 C10 . 1.387(4) ?
C9 C12 . 1.478(4) ?
C10 C11 . 1.379(5) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
C12 C13 . 1.381(5) ?
C12 C16 . 1.386(5) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.375(5) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.365(5) ?
C15 H15A . 0.9300 ?
C16 H16A . 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
N1 H1A N4 2_556 0.8600 2.4700 3.214(4) 145.00
N1 H1B N2 3_567 0.8600 2.4300 3.166(4) 144.00
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
C7 C2 C3 C4 . . . . -2.5(5) ?
C1 C2 C3 C4 . . . . 178.0(3) ?
C2 C3 C4 C5 . . . . 0.0(5) ?
C3 C4 C5 N1 . . . . -179.2(3) ?
C3 C4 C5 C6 . . . . 1.9(5) ?
C4 C5 C6 C7 . . . . -1.3(4) ?
N1 C5 C6 C7 . . . . 179.8(3) ?
C5 C6 C7 C2 . . . . -1.2(5) ?
C5 C6 C7 O . . . . -174.0(3) ?
C3 C2 C7 C6 . . . . 3.1(5) ?
C1 C2 C7 C6 . . . . -177.4(3) ?
C3 C2 C7 O . . . . 175.4(3) ?
C1 C2 C7 O . . . . -5.0(5) ?
C8 O C7 C6 . . . . -119.7(3) ?
C8 O C7 C2 . . . . 67.4(4) ?
C11 N3 C8 N2 . . . . 1.9(5) ?
C11 N3 C8 O . . . . 179.5(3) ?
C9 N2 C8 N3 . . . . -0.8(5) ?
C9 N2 C8 O . . . . -178.5(3) ?
C7 O C8 N3 . . . . 10.9(5) ?
C7 O C8 N2 . . . . -171.2(3) ?
C8 N2 C9 C10 . . . . -0.8(5) ?
C8 N2 C9 C12 . . . . 179.5(3) ?
N2 C9 C10 C11 . . . . 1.1(5) ?
C12 C9 C10 C11 . . . . -179.2(3) ?
C8 N3 C11 C10 . . . . -1.5(5) ?
C9 C10 C11 N3 . . . . 0.1(6) ?
N2 C9 C12 C13 . . . . 34.5(4) ?
C10 C9 C12 C13 . . . . -145.2(3) ?
N2 C9 C12 C16 . . . . -145.1(3) ?
C10 C9 C12 C16 . . . . 35.2(5) ?
C14 N4 C13 C12 . . . . 0.1(5) ?
C16 C12 C13 N4 . . . . 0.2(5) ?
C9 C12 C13 N4 . . . . -179.3(3) ?
C13 N4 C14 C15 . . . . -0.3(6) ?
N4 C14 C15 C16 . . . . 0.0(6) ?
C14 C15 C16 C12 . . . . 0.4(6) ?
C13 C12 C16 C15 . . . . -0.5(5) ?
C9 C12 C16 C15 . . . . 179.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742673
