#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/20/2232005.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_2232005
loop_
_publ_author_name
'Shi, Fuqiang'
'Zhu, Li-Hong'
'Mu, Li'
'Zhang, Long'
'Li, Ya-Feng'
_publ_section_title
;
 6-Chloro-N-methyl-5-nitro-N-phenylpyrimidin-4-amine
;
_journal_coeditor_code           NG5229
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2689
_journal_paper_doi               10.1107/S1600536811037664
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H9 Cl N4 O2'
_chemical_formula_moiety         'C11 H9 Cl N4 O2'
_chemical_formula_sum            'C11 H9 Cl N4 O2'
_chemical_formula_weight         264.67
_chemical_name_systematic
;
6-Chloro-N-methyl-5-nitro-N-phenylpyrimidin-4-amine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.76(3)
_cell_angle_beta                 86.80(3)
_cell_angle_gamma                84.21(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8980(14)
_cell_length_b                   8.9282(18)
_cell_length_c                   11.427(2)
_cell_measurement_reflns_used    500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.40
_cell_volume                     671.9(2)
_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 0.991
_diffrn_measured_fraction_theta_max 0.890
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5925
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0492
_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)+(0.0827P)²+0.0097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                1742
_reflns_number_total             2730
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5229.cif
_cod_data_source_block           I
_cod_original_cell_volume        672.0(2)
_cod_database_code               2232005
_cod_database_fobs_code          2232005
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 0.27001(12) 0.38397(9) 0.55435(6) 0.0897(3) Uani d . 1 1
C C1 0.2612(3) 0.1851(3) 0.52481(19) 0.0585(5) Uani d . 1 1
C C2 0.2496(3) 0.1772(2) 0.40780(17) 0.0483(5) Uani d . 1 1
C C3 0.2386(3) 0.0133(2) 0.38625(17) 0.0485(5) Uani d . 1 1
C C4 0.2470(3) -0.1014(3) 0.59315(19) 0.0655(6) Uani d . 1 1
H H4 0.2468 -0.1895 0.6599 0.079 Uiso calc R 1 1
N N1 0.2346(3) -0.1270(2) 0.48527(16) 0.0600(5) Uani d . 1 1
N N2 0.2610(3) 0.0465(3) 0.62119(16) 0.0694(6) Uani d . 1 1
C C5 0.2510(3) 0.1072(2) 0.16239(18) 0.0544(5) Uani d . 1 1
C C6 0.4329(4) 0.1522(3) 0.1186(2) 0.0716(7) Uani d . 1 1
H H6 0.5428 0.1063 0.1631 0.086 Uiso calc R 1 1
C C7 0.4528(5) 0.2692(4) 0.0051(3) 0.0954(9) Uani d . 1 1
H H7 0.5759 0.3000 -0.0227 0.114 Uiso calc R 1 1
C C8 0.2935(6) 0.3371(4) -0.0638(2) 0.1037(11) Uani d . 1 1
H H8 0.3077 0.4122 -0.1381 0.124 Uiso calc R 1 1
C C9 0.1135(6) 0.2917(4) -0.0205(3) 0.1034(11) Uani d . 1 1
H H9 0.0043 0.3376 -0.0656 0.124 Uiso calc R 1 1
C C10 0.0897(4) 0.1749(3) 0.0930(2) 0.0817(8) Uani d . 1 1
H H10 -0.0337 0.1445 0.1202 0.098 Uiso calc R 1 1
C C11 0.2102(5) -0.1969(3) 0.2719(3) 0.0965(10) Uani d . 1 1
H H11A 0.3338 -0.2570 0.2895 0.145 Uiso calc R 1 1
H H11B 0.1728 -0.1948 0.1917 0.145 Uiso calc R 1 1
H H11C 0.1136 -0.2440 0.3307 0.145 Uiso calc R 1 1
N N4 0.2395(3) 0.3422(2) 0.31108(16) 0.0611(5) Uani d . 1 1
N N3 0.2279(3) -0.0184(2) 0.27815(15) 0.0610(5) Uani d . 1 1
O O1 0.0799(3) 0.4051(2) 0.27365(17) 0.0885(6) Uani d . 1 1
O O2 0.3903(3) 0.4091(2) 0.27659(17) 0.0889(6) 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'
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
C2 C1 N2 119.2(2)
C2 C1 Cl1 119.29(17)
N2 C1 Cl1 121.46(16)
C1 C2 C3 118.29(17)
C1 C2 N4 113.29(18)
C3 C2 N4 128.35(16)
N3 C3 N1 110.90(18)
N3 C3 C2 127.02(16)
N1 C3 C2 122.06(17)
N1 C4 N2 128.60(19)
N1 C4 H4 115.7
N2 C4 H4 115.7
C4 N1 C3 112.86(19)
C1 N2 C4 118.93(18)
C6 C5 C10 118.8(2)
C6 C5 N3 121.0(2)
C10 C5 N3 120.1(2)
C5 C6 C7 120.2(2)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 121.2(3)
C8 C7 H7 119.4
C6 C7 H7 119.4
C9 C8 C7 118.4(2)
C9 C8 H8 120.8
C7 C8 H8 120.8
C8 C9 C10 121.4(3)
C8 C9 H9 119.3
C10 C9 H9 119.3
C5 C10 C9 120.0(3)
C5 C10 H10 120.0
C9 C10 H10 120.0
N3 C11 H11A 109.5
N3 C11 H11B 109.5
H11A C11 H11B 109.5
N3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O1 N4 O2 120.9(2)
O1 N4 C2 118.81(18)
O2 N4 C2 120.25(19)
C3 N3 C5 120.02(17)
C3 N3 C11 120.80(17)
C5 N3 C11 118.93(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.905(2)
C1 C2 1.366(3)
C1 N2 1.408(3)
C2 C3 1.560(3)
C2 N4 1.573(3)
C3 N3 1.349(3)
C3 N1 1.436(2)
C4 N1 1.324(3)
C4 N2 1.456(3)
C4 H4 0.9300
C5 C6 1.380(3)
C5 C10 1.388(3)
C5 N3 1.488(3)
C6 C7 1.430(4)
C6 H6 0.9300
C7 C8 1.375(5)
C7 H7 0.9300
C8 C9 1.368(4)
C8 H8 0.9300
C9 C10 1.431(4)
C9 H9 0.9300
C10 H10 0.9300
C11 N3 1.633(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
N4 O1 1.226(2)
N4 O2 1.242(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12031730
