#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/28/2232800.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_2232800
loop_
_publ_author_name
'Shi, Fuqiang'
'Zhu, Li-Hong'
'Mu, Li'
'Zhang, Long'
'Li, Ya-Feng'
_publ_section_title
;
 N⁴,N⁶-Dimethyl-N⁴,N⁶-diphenylpyrimidine-4,5,6-triamine
;
_journal_coeditor_code           IS2800
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3249
_journal_paper_doi               10.1107/S1600536811046642
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H19 N5'
_chemical_formula_moiety         'C18 H19 N5'
_chemical_formula_sum            'C18 H19 N5'
_chemical_formula_weight         305.38
_chemical_name_systematic
;
N⁴,N⁶-Dimethyl-N⁴,N⁶-
diphenylpyrimidine-4,5,6-triamine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.8859(18)
_cell_length_b                   14.360(3)
_cell_length_c                   25.121(5)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.15
_cell_volume                     3205.5(11)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2000)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            28152
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0524
_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)+(0.0693P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                2119
_reflns_number_total             3664
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2800.cif
_cod_data_source_block           I
_cod_original_cell_volume        3205.4(11)
_cod_database_code               2232800
_cod_database_fobs_code          2232800
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C C1 -0.0279(3) 0.46280(13) 0.41196(8) 0.0660(6) Uani d . 1 1
H H1 -0.0833 0.5128 0.4249 0.079 Uiso calc R 1 1
C C2 0.0751(2) 0.32120(11) 0.42746(6) 0.0483(4) Uani d . 1 1
C C3 0.15006(19) 0.32587(11) 0.37827(6) 0.0460(4) Uani d . 1 1
C C4 0.1152(2) 0.40201(11) 0.34631(6) 0.0484(4) Uani d . 1 1
C C5 0.1622(2) 0.34917(11) 0.25472(6) 0.0480(4) Uani d . 1 1
C C6 0.0766(2) 0.26882(12) 0.26084(7) 0.0563(5) Uani d . 1 1
H H6 0.0287 0.2573 0.2931 0.068 Uiso calc R 1 1
C C7 0.0620(2) 0.20590(13) 0.21954(8) 0.0626(5) Uani d . 1 1
H H7 0.0059 0.1519 0.2245 0.075 Uiso calc R 1 1
C C8 0.1296(2) 0.22228(16) 0.17087(8) 0.0689(6) Uani d . 1 1
H H8 0.1205 0.1795 0.1433 0.083 Uiso calc R 1 1
C C9 0.2099(2) 0.30237(15) 0.16412(8) 0.0679(6) Uani d . 1 1
H H9 0.2534 0.3148 0.1312 0.082 Uiso calc R 1 1
C C10 0.2278(2) 0.36518(14) 0.20496(7) 0.0586(5) Uani d . 1 1
H H10 0.2842 0.4189 0.1994 0.070 Uiso calc R 1 1
C C11 0.0814(2) 0.15421(10) 0.44409(6) 0.0478(4) Uani d . 1 1
C C12 0.1647(2) 0.08195(13) 0.46579(7) 0.0612(5) Uani d . 1 1
H H12 0.2369 0.0943 0.4917 0.073 Uiso calc R 1 1
C C13 0.1404(3) -0.00819(13) 0.44895(9) 0.0713(6) Uani d . 1 1
H H13 0.1949 -0.0566 0.4642 0.086 Uiso calc R 1 1
C C14 0.0367(3) -0.02727(13) 0.40991(9) 0.0732(6) Uani d . 1 1
H H14 0.0223 -0.0882 0.3983 0.088 Uiso calc R 1 1
C C15 -0.0447(3) 0.04322(13) 0.38829(8) 0.0688(6) Uani d . 1 1
H H15 -0.1150 0.0305 0.3619 0.083 Uiso calc R 1 1
C C16 -0.0238(2) 0.13385(12) 0.40531(7) 0.0570(5) Uani d . 1 1
H H16 -0.0810 0.1815 0.3905 0.068 Uiso calc R 1 1
C C17 0.2467(3) 0.50505(12) 0.28371(9) 0.0743(6) Uani d . 1 1
H H17A 0.3482 0.4977 0.2713 0.111 Uiso calc R 1 1
H H17B 0.2464 0.5430 0.3152 0.111 Uiso calc R 1 1
H H17C 0.1874 0.5345 0.2566 0.111 Uiso calc R 1 1
C C18 0.0744(4) 0.26304(14) 0.51905(7) 0.0931(9) Uani d . 1 1
H H18A 0.1106 0.3236 0.5290 0.140 Uiso calc R 1 1
H H18B 0.1257 0.2163 0.5395 0.140 Uiso calc R 1 1
H H18C -0.0318 0.2593 0.5258 0.140 Uiso calc R 1 1
N N1 0.02716(19) 0.47211(9) 0.36360(6) 0.0593(4) Uani d . 1 1
N N2 -0.01344(19) 0.39000(10) 0.44460(6) 0.0602(4) Uani d . 1 1
N N3 0.18291(19) 0.41347(9) 0.29607(6) 0.0578(4) Uani d . 1 1
N N4 0.25718(18) 0.26103(9) 0.36391(6) 0.0583(4) Uani d . 1 1
H H4A 0.3049 0.2669 0.3343 0.070 Uiso calc R 1 1
H H4B 0.2762 0.2147 0.3845 0.070 Uiso calc R 1 1
N N5 0.1029(2) 0.24762(9) 0.46223(5) 0.0568(4) Uani 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 N2 127.64(17)
N1 C1 H1 116.2
N2 C1 H1 116.2
N2 C2 N5 117.64(15)
N2 C2 C3 121.86(15)
N5 C2 C3 120.22(15)
N4 C3 C4 122.23(15)
N4 C3 C2 121.66(15)
C4 C3 C2 116.04(15)
N1 C4 C3 122.05(15)
N1 C4 N3 116.75(14)
C3 C4 N3 120.91(16)
C6 C5 C10 117.61(16)
C6 C5 N3 122.42(15)
C10 C5 N3 119.97(16)
C7 C6 C5 120.74(17)
C7 C6 H6 119.6
C5 C6 H6 119.6
C6 C7 C8 120.78(19)
C6 C7 H7 119.6
C8 C7 H7 119.6
C9 C8 C7 118.74(18)
C9 C8 H8 120.6
C7 C8 H8 120.6
C8 C9 C10 121.40(19)
C8 C9 H9 119.3
C10 C9 H9 119.3
C9 C10 C5 120.70(19)
C9 C10 H10 119.7
C5 C10 H10 119.7
C16 C11 C12 118.70(16)
C16 C11 N5 120.91(15)
C12 C11 N5 120.38(16)
C13 C12 C11 119.90(19)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 120.75(19)
C14 C13 H13 119.6
C12 C13 H13 119.6
C15 C14 C13 119.64(19)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C16 120.4(2)
C14 C15 H15 119.8
C16 C15 H15 119.8
C11 C16 C15 120.57(17)
C11 C16 H16 119.7
C15 C16 H16 119.7
N3 C17 H17A 109.5
N3 C17 H17B 109.5
H17A C17 H17B 109.5
N3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N5 C18 H18A 109.5
N5 C18 H18B 109.5
H18A C18 H18B 109.5
N5 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C1 N1 C4 115.94(15)
C2 N2 C1 116.00(16)
C5 N3 C4 122.09(14)
C5 N3 C17 118.99(15)
C4 N3 C17 117.41(14)
C3 N4 H4A 120.0
C3 N4 H4B 120.0
H4A N4 H4B 120.0
C2 N5 C11 119.23(13)
C2 N5 C18 117.72(15)
C11 N5 C18 115.39(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.316(2)
C1 N2 1.335(2)
C1 H1 0.9300
C2 N2 1.334(2)
C2 N5 1.393(2)
C2 C3 1.406(2)
C3 N4 1.379(2)
C3 C4 1.391(2)
C4 N1 1.347(2)
C4 N3 1.408(2)
C5 C6 1.391(2)
C5 C10 1.398(2)
C5 N3 1.402(2)
C6 C7 1.382(2)
C6 H6 0.9300
C7 C8 1.382(3)
C7 H7 0.9300
C8 C9 1.364(3)
C8 H8 0.9300
C9 C10 1.375(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C16 1.381(2)
C11 C12 1.386(2)
C11 N5 1.429(2)
C12 C13 1.379(3)
C12 H12 0.9300
C13 C14 1.374(3)
C13 H13 0.9300
C14 C15 1.357(3)
C14 H14 0.9300
C15 C16 1.383(2)
C15 H15 0.9300
C16 H16 0.9300
C17 N3 1.465(2)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 N5 1.466(2)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
N4 H4A 0.8600
N4 H4B 0.8600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12084802
