#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/65/2206523.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_2206523
loop_
_publ_author_name
'Li, Yang'
'Ding, Li'
'Zeng, Tao'
'Li, Jiang-Sheng'
'Dong, Chuan-Ming'
'Yan, Xi-Long'
_publ_section_title
;
 N-(4-Chloro-6-morpholino-1,3,5-triazin-2-yl)aniline
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2345
_journal_page_last               o2346
_journal_paper_doi               10.1107/S1600536805020040
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C13 H14 Cl N5 O'
_chemical_formula_moiety         'C13 H14 Cl N5 O'
_chemical_formula_sum            'C13 H14 Cl N5 O'
_chemical_formula_weight         291.74
_chemical_name_systematic
;
N-(4-Chloro-6-morpholino-1,3,5-triazin-2-yl)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
_cell_angle_alpha                90.00
_cell_angle_beta                 108.860(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3481(15)
_cell_length_b                   17.667(3)
_cell_length_c                   9.9401(18)
_cell_measurement_reflns_used    2305
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.69
_cell_measurement_theta_min      2.45
_cell_volume                     1387.3(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7720
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0414P)²+0.3828P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                1842
_reflns_number_total             2831
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rn6054.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206523
_cod_database_fobs_code          2206523
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_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_type_symbol
Cl1 0.03671(9) 0.71046(3) 0.67396(7) 0.0706(2) Uani d . 1 Cl
O1 0.24332(19) 0.50541(8) 0.10247(14) 0.0547(4) Uani d . 1 O
N1 0.2337(2) 0.53716(9) 0.37647(15) 0.0436(4) Uani d . 1 N
N2 0.1458(2) 0.61879(9) 0.52006(16) 0.0421(4) Uani d . 1 N
N3 0.1653(2) 0.57833(9) 0.75298(16) 0.0448(4) Uani d . 1 N
N4 0.24573(19) 0.49394(9) 0.59761(15) 0.0392(4) Uani d . 1 N
N5 0.2697(2) 0.46120(10) 0.82896(17) 0.0474(5) Uani d . 1 N
H5 0.269(3) 0.4789(11) 0.907(2) 0.049(6) Uiso d . 1 H
C1 0.3084(3) 0.46662(12) 0.3481(2) 0.0478(5) Uani d . 1 C
H1A 0.2898 0.4266 0.4083 0.057 Uiso calc R 1 H
H1B 0.4294 0.4730 0.3693 0.057 Uiso calc R 1 H
C2 0.2283(3) 0.44540(12) 0.1941(2) 0.0532(6) Uani d . 1 C
H2A 0.2827 0.4003 0.1737 0.064 Uiso calc R 1 H
H2B 0.1095 0.4339 0.1759 0.064 Uiso calc R 1 H
C3 0.1589(3) 0.57112(13) 0.1274(2) 0.0541(6) Uani d . 1 C
H3A 0.0401 0.5597 0.1090 0.065 Uiso calc R 1 H
H3B 0.1666 0.6108 0.0624 0.065 Uiso calc R 1 H
C4 0.2345(3) 0.59873(12) 0.2776(2) 0.0521(6) Uani d . 1 C
H4A 0.3497 0.6157 0.2936 0.063 Uiso calc R 1 H
H4B 0.1694 0.6412 0.2938 0.063 Uiso calc R 1 H
C5 0.2082(2) 0.55015(10) 0.50159(18) 0.0354(4) Uani d . 1 C
C6 0.1274(2) 0.62567(11) 0.6455(2) 0.0429(5) Uani d . 1 C
C7 0.2258(2) 0.51160(11) 0.72146(19) 0.0388(4) Uani d . 1 C
C8 0.3381(2) 0.38802(11) 0.8287(2) 0.0421(5) Uani d . 1 C
C9 0.4687(3) 0.36449(14) 0.9467(2) 0.0560(6) Uani d . 1 C
H9 0.5109 0.3968 1.0239 0.067 Uiso calc R 1 H
C10 0.5367(3) 0.29285(16) 0.9499(3) 0.0713(7) Uani d . 1 C
H10 0.6242 0.2771 1.0297 0.086 Uiso calc R 1 H
C11 0.4761(3) 0.24493(15) 0.8366(3) 0.0724(7) Uani d . 1 C
H11 0.5230 0.1970 0.8387 0.087 Uiso calc R 1 H
C12 0.3453(3) 0.26819(13) 0.7194(3) 0.0663(7) Uani d . 1 C
H12 0.3041 0.2358 0.6422 0.080 Uiso calc R 1 H
C13 0.2749(3) 0.33895(12) 0.7156(2) 0.0523(5) Uani d . 1 C
H13 0.1848 0.3537 0.6369 0.063 Uiso calc R 1 H
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'
Cl Cl 0.1484 0.1585 '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
C3 O1 C2 110.13(15)
C5 N1 C1 121.87(15)
C5 N1 C4 121.87(16)
C1 N1 C4 114.11(15)
C6 N2 C5 112.35(16)
C6 N3 C7 112.02(16)
C7 N4 C5 114.45(16)
C7 N5 C8 127.52(16)
C7 N5 H5 113.9(14)
C8 N5 H5 117.8(14)
N1 C1 C2 109.37(17)
N1 C1 H1A 109.8
C2 C1 H1A 109.8
N1 C1 H1B 109.8
C2 C1 H1B 109.8
H1A C1 H1B 108.2
O1 C2 C1 111.17(17)
O1 C2 H2A 109.4
C1 C2 H2A 109.4
O1 C2 H2B 109.4
C1 C2 H2B 109.4
H2A C2 H2B 108.0
O1 C3 C4 111.49(17)
O1 C3 H3A 109.3
C4 C3 H3A 109.3
O1 C3 H3B 109.3
C4 C3 H3B 109.3
H3A C3 H3B 108.0
N1 C4 C3 109.48(17)
N1 C4 H4A 109.8
C3 C4 H4A 109.8
N1 C4 H4B 109.8
C3 C4 H4B 109.8
H4A C4 H4B 108.2
N4 C5 N1 117.39(16)
N4 C5 N2 125.25(16)
N1 C5 N2 117.36(16)
N2 C6 N3 130.09(19)
N2 C6 Cl1 115.14(16)
N3 C6 Cl1 114.77(14)
N4 C7 N5 119.69(18)
N4 C7 N3 125.69(17)
N5 C7 N3 114.61(16)
C13 C8 C9 119.4(2)
C13 C8 N5 121.82(18)
C9 C8 N5 118.78(19)
C8 C9 C10 120.0(2)
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 120.5(2)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 119.5(2)
C10 C11 H11 120.2
C12 C11 H11 120.2
C13 C12 C11 120.6(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C8 120.0(2)
C12 C13 H13 120.0
C8 C13 H13 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C6 1.742(2)
O1 C3 1.421(3)
O1 C2 1.429(2)
N1 C5 1.348(2)
N1 C1 1.461(2)
N1 C4 1.467(2)
N2 C6 1.311(2)
N2 C5 1.355(2)
N3 C6 1.312(2)
N3 C7 1.359(2)
N4 C7 1.331(2)
N4 C5 1.342(2)
N5 C7 1.348(2)
N5 C8 1.414(3)
N5 H5 0.84(2)
C1 C2 1.507(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.502(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 H4A 0.9700
C4 H4B 0.9700
C8 C13 1.382(3)
C8 C9 1.383(3)
C9 C10 1.383(3)
C9 H9 0.9300
C10 C11 1.368(4)
C10 H10 0.9300
C11 C12 1.377(3)
C11 H11 0.9300
C12 C13 1.377(3)
C12 H12 0.9300
C13 H13 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
N5 H5 O1 1_556 0.84(2) 2.08(2) 2.905(2) 170(2)
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
C5 N1 C1 C2 144.77(18)
C4 N1 C1 C2 -51.6(2)
C3 O1 C2 C1 -61.1(2)
N1 C1 C2 O1 55.5(2)
C2 O1 C3 C4 61.0(2)
C5 N1 C4 C3 -144.97(19)
C1 N1 C4 C3 51.4(2)
O1 C3 C4 N1 -55.2(2)
C7 N4 C5 N1 176.78(17)
C7 N4 C5 N2 -3.6(3)
C1 N1 C5 N4 -3.5(3)
C4 N1 C5 N4 -165.84(17)
C1 N1 C5 N2 176.88(17)
C4 N1 C5 N2 14.5(3)
C6 N2 C5 N4 1.0(3)
C6 N2 C5 N1 -179.40(17)
C5 N2 C6 N3 2.7(3)
C5 N2 C6 Cl1 -176.58(13)
C7 N3 C6 N2 -3.1(3)
C7 N3 C6 Cl1 176.26(13)
C5 N4 C7 N5 -175.90(17)
C5 N4 C7 N3 3.2(3)
C8 N5 C7 N4 0.1(3)
C8 N5 C7 N3 -179.10(18)
C6 N3 C7 N4 -0.3(3)
C6 N3 C7 N5 178.88(17)
C7 N5 C8 C13 -43.9(3)
C7 N5 C8 C9 137.9(2)
C13 C8 C9 C10 1.0(3)
N5 C8 C9 C10 179.3(2)
C8 C9 C10 C11 0.3(4)
C9 C10 C11 C12 -0.7(4)
C10 C11 C12 C13 -0.2(4)
C11 C12 C13 C8 1.5(4)
C9 C8 C13 C12 -1.9(3)
N5 C8 C13 C12 179.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 731197
