#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/63/2236390.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_2236390
loop_
_publ_author_name
'Thanigaimani, Kaliyaperumal'
'Razak, Ibrahim Abdul'
'Arshad, Suhana'
'Jagatheesan, Rathinavel'
'Santhanaraj, K. Joseph'
_publ_section_title
;
 6-(4-Methoxyphenyl)-1,3,5-triazine-2,4-diamine
;
_journal_coeditor_code           IS5191
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2910
_journal_paper_doi               10.1107/S1600536812038019
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H11 N5 O'
_chemical_formula_moiety         'C10 H11 N5 O'
_chemical_formula_sum            'C10 H11 N5 O'
_chemical_formula_weight         217.24
_chemical_name_systematic
;
6-(4-Methoxyphenyl)-1,3,5-triazine-2,4-diamine
;
_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                 114.1910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4340(2)
_cell_length_b                   10.0355(3)
_cell_length_c                   14.6803(4)
_cell_measurement_reflns_used    7910
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      32.46
_cell_measurement_theta_min      2.54
_cell_volume                     999.03(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16310
_diffrn_reflns_theta_full        32.59
_diffrn_reflns_theta_max         32.59
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0407
_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)+(0.0686P)²+0.2052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                3112
_reflns_number_total             3611
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5191.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236390
_cod_database_fobs_code          2236390
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
O O1 0.35597(9) 0.64750(7) 0.95775(5) 0.01650(14) Uani d . 1 1
N N1 0.89236(10) 0.73352(7) 0.71745(5) 0.01370(14) Uani d . 1 1
N N2 1.14046(11) 0.80754(8) 0.67477(6) 0.01588(15) Uani d . 1 1
N N3 0.98420(10) 0.61218(7) 0.60228(5) 0.01364(14) Uani d . 1 1
N N4 0.81934(12) 0.41721(8) 0.53671(6) 0.01771(16) Uani d . 1 1
N N5 0.74625(11) 0.52210(7) 0.65619(5) 0.01434(15) Uani d . 1 1
C C2 1.00276(12) 0.71420(8) 0.66483(6) 0.01287(15) Uani d . 1 1
C C4 0.85102(12) 0.51935(8) 0.59951(6) 0.01342(15) Uani d . 1 1
C C6 0.76980(11) 0.63268(8) 0.71082(6) 0.01251(15) Uani d . 1 1
C C7 0.65370(12) 0.63948(8) 0.77219(6) 0.01286(15) Uani d . 1 1
C C8 0.50541(12) 0.54629(9) 0.75799(6) 0.01468(16) Uani d . 1 1
H H8A 0.4749 0.4824 0.7061 0.018 Uiso calc R 1 1
C C9 0.40092(12) 0.54448(8) 0.81785(6) 0.01421(16) Uani d . 1 1
H H9A 0.3015 0.4796 0.8078 0.017 Uiso calc R 1 1
C C10 0.44520(12) 0.63999(8) 0.89293(6) 0.01308(15) Uani d . 1 1
C C11 0.59087(12) 0.73581(9) 0.90702(6) 0.01452(16) Uani d . 1 1
H H11A 0.6182 0.8016 0.9575 0.017 Uiso calc R 1 1
C C12 0.69527(12) 0.73512(8) 0.84777(6) 0.01394(16) Uani d . 1 1
H H12A 0.7954 0.7996 0.8583 0.017 Uiso calc R 1 1
C C13 0.19727(13) 0.55633(10) 0.94259(7) 0.01802(17) Uani d . 1 1
H H13A 0.1488 0.5697 0.9947 0.027 Uiso calc R 1 1
H H13B 0.2448 0.4646 0.9457 0.027 Uiso calc R 1 1
H H13C 0.0900 0.5724 0.8770 0.027 Uiso calc R 1 1
H H2A 1.236(2) 0.7853(15) 0.6551(11) 0.031(4) Uiso d . 1 1
H H2B 1.1747(19) 0.8611(14) 0.7264(10) 0.023(3) Uiso d . 1 1
H H4A 0.882(2) 0.4077(15) 0.4965(11) 0.029(3) Uiso d . 1 1
H H4B 0.739(2) 0.3525(15) 0.5360(11) 0.030(4) Uiso d . 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'
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
C10 O1 C13 117.33(7)
C6 N1 C2 113.87(7)
C2 N2 H2A 117.2(10)
C2 N2 H2B 117.2(9)
H2A N2 H2B 116.3(13)
C2 N3 C4 114.56(7)
C4 N4 H4A 123.0(10)
C4 N4 H4B 120.3(9)
H4A N4 H4B 116.6(13)
C6 N5 C4 114.75(7)
N3 C2 N2 117.59(7)
N3 C2 N1 125.68(7)
N2 C2 N1 116.72(7)
N4 C4 N3 118.14(7)
N4 C4 N5 117.24(7)
N3 C4 N5 124.62(8)
N5 C6 N1 126.06(7)
N5 C6 C7 115.89(7)
N1 C6 C7 118.00(7)
C8 C7 C12 118.78(7)
C8 C7 C6 119.98(7)
C12 C7 C6 121.18(7)
C9 C8 C7 121.75(8)
C9 C8 H8A 119.1
C7 C8 H8A 119.1
C8 C9 C10 118.57(8)
C8 C9 H9A 120.7
C10 C9 H9A 120.7
O1 C10 C9 124.29(7)
O1 C10 C11 115.23(7)
C9 C10 C11 120.47(7)
C12 C11 C10 120.24(8)
C12 C11 H11A 119.9
C10 C11 H11A 119.9
C11 C12 C7 120.17(8)
C11 C12 H12A 119.9
C7 C12 H12A 119.9
O1 C13 H13A 109.5
O1 C13 H13B 109.5
H13A C13 H13B 109.5
O1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.3669(10)
O1 C13 1.4364(11)
N1 C6 1.3384(11)
N1 C2 1.3517(10)
N2 C2 1.3507(11)
N2 H2A 0.896(15)
N2 H2B 0.877(14)
N3 C2 1.3441(11)
N3 C4 1.3479(11)
N4 C4 1.3335(11)
N4 H4A 0.896(15)
N4 H4B 0.878(15)
N5 C6 1.3380(11)
N5 C4 1.3530(10)
C6 C7 1.4826(11)
C7 C8 1.3946(12)
C7 C12 1.4025(12)
C8 C9 1.3911(11)
C8 H8A 0.9500
C9 C10 1.3945(12)
C9 H9A 0.9500
C10 C11 1.3988(12)
C11 C12 1.3828(11)
C11 H11A 0.9500
C12 H12A 0.9500
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
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 H2B N5 2_756 0.878(14) 2.258(14) 3.1291(11) 172.1(12) yes
N4 H4A N3 3_766 0.894(16) 2.077(16) 2.9708(12) 177.4(14) yes
N4 H4B O1 2_646 0.879(16) 2.189(15) 3.0196(11) 157.3(14) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 32140
