#------------------------------------------------------------------------------ #$Date: 2011-01-02 20:00:31 +0000 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203202.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_2203202 loop_ _publ_author_name 'Declan McKeveney' 'Ronald J. Quinn' 'Christian O. Janssen' 'Peter C. Healy' _publ_section_title ; 4-Amino-2,6-dichloro-5-nitropyrimidine ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o241 _journal_page_last o243 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C4 H2 Cl2 N4 O2' _chemical_formula_moiety 'C4 H2 Cl2 N4 O2' _chemical_formula_sum 'C4 H2 Cl2 N4 O2' _chemical_formula_weight 209.00 _chemical_name_systematic ; 4-amino-2,6-dichloro-5-nitropyrimidine ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 116.608(15) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 17.667(3) _cell_length_b 6.708(2) _cell_length_c 14.425(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 17.0 _cell_measurement_theta_min 12.6 _cell_volume 1528.5(6) _computing_cell_refinement 'MSC/AFC7 Diffractometer Control Software' _computing_data_collection ; MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999) ; _computing_data_reduction 'TEXSAN for Windows (Molecular Structure Corporation, 1997-2001)' _computing_molecular_graphics 'PLATON (Spek, 1980-2001) and ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'TEXSAN for Windows and PLATON' _computing_structure_refinement 'TEXSAN for Windows and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'TEXSAN for Windows' _diffrn_ambient_temperature 295 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'Rigaku AFC-7R' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2123 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.58 _diffrn_standards_decay_% 0.68 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.809 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.816 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 832 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.573 _refine_diff_density_min -0.398 _refine_ls_extinction_coef 0.0046(10) _refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 1766 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0473 _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/[\s^2^(Fo^2^)+(0.0646P)^2^+2.5264P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1289 _refine_ls_wR_factor_ref 0.1441 _reflns_number_gt 1290 _reflns_number_total 1766 _reflns_threshold_expression I>2\s(I) _[local]_cod_cif_authors_sg_H-M 'C 2/c' _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 ; _cod_database_code 2203202 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl2 0.0595(5) 0.0763(6) 0.0708(6) 0.0302(4) 0.0420(4) 0.0178(4) Cl6 0.0714(6) 0.0762(6) 0.1017(8) 0.0104(5) 0.0614(6) 0.0280(5) O51 0.099(2) 0.080(2) 0.163(3) 0.0484(18) 0.096(2) 0.050(2) O52 0.0528(14) 0.092(2) 0.123(2) 0.0061(14) 0.0523(16) 0.0049(18) N1 0.0536(15) 0.0525(15) 0.0631(16) 0.0134(12) 0.0360(13) 0.0100(12) N3 0.0420(12) 0.0520(14) 0.0482(13) 0.0078(10) 0.0273(11) 0.0019(11) N4 0.0625(17) 0.0569(16) 0.081(2) 0.0158(13) 0.0492(16) 0.0172(14) N5 0.0427(13) 0.0639(17) 0.0521(14) 0.0101(12) 0.0273(11) 0.0022(12) C2 0.0420(14) 0.0546(17) 0.0464(15) 0.0100(12) 0.0246(12) 0.0004(13) C4 0.0438(14) 0.0485(16) 0.0441(14) 0.0047(12) 0.0238(12) 0.0007(12) C5 0.0375(13) 0.0496(15) 0.0451(14) 0.0041(11) 0.0233(12) -0.0033(12) C6 0.0458(15) 0.0505(17) 0.0526(16) 0.0002(12) 0.0300(13) -0.0002(13) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol Cl2 0.33745(5) -0.22273(15) 0.63602(7) 0.0641(3) Uani 1.000 Cl Cl6 0.09354(6) -0.20427(16) 0.73648(9) 0.0746(4) Uani 1.000 Cl O51 0.0276(2) 0.3556(5) 0.5830(3) 0.1001(14) Uani 1.000 O O52 -0.01950(16) 0.0785(5) 0.6049(3) 0.0844(11) Uani 1.000 O N1 0.21172(16) -0.1855(4) 0.6805(2) 0.0527(9) Uani 1.000 N N3 0.23196(14) 0.0673(4) 0.57753(18) 0.0447(8) Uani 1.000 N N4 0.14712(18) 0.3373(4) 0.5180(2) 0.0604(10) Uani 1.000 N N5 0.03583(15) 0.1792(4) 0.6017(2) 0.0506(9) Uani 1.000 N C2 0.24977(17) -0.0985(5) 0.6304(2) 0.0459(9) Uani 1.000 C C4 0.16328(18) 0.1691(4) 0.5706(2) 0.0439(8) Uani 1.000 C C5 0.11425(16) 0.0847(4) 0.6166(2) 0.0423(8) Uani 1.000 C C6 0.14259(18) -0.0922(5) 0.6713(2) 0.0467(9) Uani 1.000 C H41 0.10460 0.40930 0.51140 0.0720 Uiso 1.000 H H42 0.17940 0.37700 0.49150 0.0720 Uiso 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -1 -3 -1 -1 -2 0 0 -4 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 N1 C6 114.1(3) yes C2 N3 C4 116.5(3) yes O51 N5 O52 122.6(3) yes O51 N5 C5 118.2(3) yes O52 N5 C5 119.1(3) yes H41 N4 H42 119.79 no C4 N4 H41 119.79 no C4 N4 H42 120.40 no Cl2 C2 N3 114.5(2) yes Cl2 C2 N1 115.2(2) yes N1 C2 N3 130.3(3) yes N3 C4 N4 115.4(3) yes N3 C4 C5 118.5(2) yes N4 C4 C5 126.1(3) yes C4 C5 C6 117.7(3) no N5 C5 C4 119.9(2) yes N5 C5 C6 122.4(3) yes Cl6 C6 N1 114.1(2) yes Cl6 C6 C5 123.0(3) yes N1 C6 C5 122.8(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl2 C2 1.729(3) yes Cl6 C6 1.712(3) yes O51 N5 1.208(4) yes O52 N5 1.206(4) yes N1 C2 1.323(4) yes N1 C6 1.325(5) yes N3 C2 1.305(4) yes N3 C4 1.356(4) yes N4 C4 1.318(4) yes N5 C5 1.449(4) yes N4 H42 0.8588 no N4 H41 0.8617 no C4 C5 1.423(4) yes C5 C6 1.388(4) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl2 O52 3.063(4) 5_545 no Cl2 Cl6 3.6462(18) 6_546 no Cl2 N5 3.489(3) 6_546 no Cl2 C5 3.522(3) 6_546 no Cl2 C6 3.621(3) 6_546 no Cl2 N4 3.498(3) 7_556 no Cl2 C2 3.644(3) 7_546 no Cl6 Cl6 3.497(2) 2_556 no Cl6 O52 2.792(4) . no Cl6 N5 3.108(3) . no Cl6 Cl2 3.6462(18) 6_556 no Cl6 N3 3.412(3) 6_546 no Cl2 H42 2.8914 7_556 no O51 N4 2.670(5) . no O51 O51 2.889(5) 3_566 no O52 Cl6 2.792(4) . no O52 C5 3.069(5) 3_556 no O52 Cl2 3.063(4) 5_455 no O52 C4 3.140(5) 3_556 no O51 H41 2.6358 3_566 no O51 H41 2.0750 . no N1 C4 3.408(4) 6_546 no N3 Cl6 3.412(3) 6_556 no N3 N4 3.084(4) 7_556 no N4 Cl2 3.498(3) 7_556 no N4 O51 2.670(5) . no N4 N5 2.928(4) . no N4 N3 3.084(4) 7_556 no N5 N4 2.928(4) . no N5 Cl6 3.108(3) . no N5 Cl2 3.489(3) 6_556 no N3 H42 2.2317 7_556 no N5 H41 2.6406 . no C2 Cl2 3.644(3) 7_546 no C4 O52 3.140(5) 3_556 no C4 N1 3.408(4) 6_556 no C5 O52 3.069(5) 3_556 no C5 Cl2 3.522(3) 6_556 no C6 Cl2 3.621(3) 6_556 no C2 H42 2.9726 7_556 no H41 O51 2.0750 . no H41 N5 2.6406 . no H41 O51 2.6358 3_566 no H42 Cl2 2.8914 7_556 no H42 N3 2.2317 7_556 no H42 C2 2.9726 7_556 no 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 N4 H41 O51 . 0.86 2.08 2.670(5) 126 no N4 H42 N3 7_556 0.86 2.23 3.084(4) 172 no 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 _geom_torsion_publ_flag C6 N1 C2 Cl2 -177.2(2) no C6 N1 C2 N3 3.2(5) no C2 N1 C6 Cl6 -179.8(2) no C2 N1 C6 C5 -2.0(4) no C4 N3 C2 Cl2 179.6(2) no C4 N3 C2 N1 -0.7(5) no C2 N3 C4 N4 179.2(3) no C2 N3 C4 C5 -2.8(4) no O51 N5 C5 C4 -25.1(4) no O51 N5 C5 C6 157.5(3) no O52 N5 C5 C4 152.4(3) no O52 N5 C5 C6 -24.9(4) no N3 C4 C5 N5 -173.8(2) no N3 C4 C5 C6 3.7(4) no N4 C4 C5 N5 4.0(4) no N4 C4 C5 C6 -178.5(3) no N5 C5 C6 N1 176.2(3) no C4 C5 C6 Cl6 176.4(2) no C4 C5 C6 N1 -1.2(4) no N5 C5 C6 Cl6 -6.2(4) no