#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011557.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_2011557 loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _publ_section_title ; 2-Amino-6-chloro-4-(1-phenylethylamino)pyrimidine ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e534 _journal_page_last e534 _journal_paper_doi 10.1107/S0108270100014177 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C12 H13 Cl N4' _chemical_formula_weight 248.71 _chemical_melting_point 415.0(10) _chemical_name_systematic ; 2-Amino-6-chloro-4-(1-phenylethylamino)pyrimidine ; _space_group_IT_number 88 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall '-I 4ad' _symmetry_space_group_name_H-M 'I 41/a :2' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 16 _cell_length_a 17.4851(7) _cell_length_b 17.4851(6) _cell_length_c 16.2878(9) _cell_measurement_reflns_used 10256 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 4979.6(4) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full .996 _diffrn_measured_fraction_theta_max .996 _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .137 _diffrn_reflns_av_sigmaI/netI .0785 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 15828 _diffrn_reflns_theta_full 27.43 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_theta_min 3.00 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .290 _exptl_absorpt_correction_T_max .972 _exptl_absorpt_correction_T_min .958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2080 _exptl_crystal_size_max .15 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .10 _refine_diff_density_max .235 _refine_diff_density_min -.354 _refine_ls_extinction_coef .0014(3) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 2828 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all .090 _refine_ls_R_factor_gt .051 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.1078P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .134 _reflns_number_gt 1893 _reflns_number_total 2828 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0429.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '414-416 K' was changed to '415.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '414-416 K' was changed to '415.0(10)' - the average value was taken and precision was estimated. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'I 41/a' _cod_database_code 2011557 _cod_database_fobs_code 2011557 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .31739(9) .31705(9) .20507(10) .0320(4) Uani d . 1 . . N C2 .36717(11) .29808(11) .26613(12) .0303(5) Uani d . 1 . . C N21 .34152(10) .24900(10) .32285(10) .0401(5) Uani d . 1 . . N H21 .3718 .2342 .3630 .050 Uiso calc R 1 . . H H22 .2944 .2315 .3200 .050 Uiso calc R 1 . . H N3 .43912(9) .32257(9) .27372(9) .0306(4) Uani d . 1 . . N C4 .46688(11) .36657(10) .21254(12) .0301(5) Uani d . 1 . . C C5 .42008(11) .38992(11) .14655(12) .0310(5) Uani d . 1 . . C H5 .4383 .4219 .1036 .039 Uiso calc R 1 . . H C6 .34694(11) .36324(11) .14893(12) .0306(5) Uani d . 1 . . C Cl6 .28398(3) .38817(3) .06998(3) .0423(2) Uani d . 1 . . Cl N41 .54094(9) .38579(9) .21952(10) .0350(4) Uani d . 1 . . N H41 .5654 .3692 .2632 .044 Uiso calc R 1 . . H C42 .58444(12) .43178(11) .16105(13) .0355(5) Uani d . 1 . . C H42 .5584 .4824 .1551 .044 Uiso calc R 1 . . H C43 .66346(13) .44519(14) .19751(15) .0485(6) Uani d . 1 . . C H431 .6584 .4704 .2509 .061 Uiso calc R 1 . . H H432 .6933 .4777 .1605 .061 Uiso calc R 1 . . H H433 .6896 .3960 .2046 .061 Uiso calc R 1 . . H C44 .59000(10) .39531(11) .07702(12) .0319(5) Uani d . 1 . . C C45 .59478(12) .44099(12) .00766(13) .0393(5) Uani d . 1 . . C H45 .5921 .4950 .0131 .049 Uiso calc R 1 . . H C46 .60340(13) .40891(13) -.06919(13) .0442(6) Uani d . 1 . . C H46 .6066 .4410 -.1161 .055 Uiso calc R 1 . . H C47 .60735(12) .33102(13) -.07838(14) .0416(6) Uani d . 1 . . C H47 .6136 .3090 -.1313 .052 Uiso calc R 1 . . H C48 .60210(13) .28490(13) -.00951(14) .0483(6) Uani d . 1 . . C H48 .6046 .2309 -.0152 .060 Uiso calc R 1 . . H C49 .59323(13) .31706(12) .06741(14) .0442(6) Uani d . 1 . . C H49 .5893 .2849 .1142 .055 Uiso calc R 1 . . H 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 N1 .0349(9) .0330(9) .0281(9) .0007(7) -.0003(7) .0028(7) C2 .0375(12) .0285(11) .0249(10) .0017(8) -.0008(8) -.0004(8) N21 .0404(11) .0489(11) .0310(10) -.0110(8) -.0057(8) .0131(8) N3 .0362(10) .0298(9) .0257(9) -.0002(7) -.0016(7) .0008(7) C4 .0352(11) .0263(10) .0287(10) .0002(8) -.0003(8) -.0037(8) C5 .0363(11) .0280(10) .0288(11) -.0014(8) -.0005(9) .0050(8) C6 .0374(11) .0261(10) .0282(10) .0032(8) -.0038(8) .0012(8) Cl6 .0395(3) .0475(4) .0399(4) .0003(2) -.0080(2) .0143(2) N41 .0362(10) .0372(10) .0315(10) -.0049(7) -.0046(7) .0037(7) C42 .0382(12) .0302(11) .0382(12) -.0047(8) .0000(9) .0032(9) C43 .0432(13) .0530(15) .0494(15) -.0159(11) -.0046(11) -.0010(12) C44 .0253(10) .0321(11) .0383(12) -.0015(8) -.0025(8) .0017(9) C45 .0439(13) .0306(11) .0435(13) -.0010(9) .0036(10) .0066(10) C46 .0498(14) .0462(14) .0366(13) .0035(10) .0014(10) .0094(10) C47 .0401(12) .0496(14) .0350(12) .0059(10) -.0011(10) -.0022(10) C48 .0622(16) .0364(13) .0463(15) .0080(10) -.0023(12) -.0011(11) C49 .0613(15) .0327(12) .0387(13) .0027(10) -.0002(11) .0064(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .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 C6 N1 C2 113.77(17) N3 C2 N21 117.23(17) N3 C2 N1 126.27(18) N21 C2 N1 116.48(18) C2 N21 H21 120.0 C2 N21 H22 120.0 H21 N21 H22 120.0 C2 N3 C4 116.97(16) N41 C4 N3 115.28(18) N41 C4 C5 123.46(18) N3 C4 C5 121.26(18) C6 C5 C4 115.07(18) C6 C5 H5 122.5 C4 C5 H5 122.5 N1 C6 C5 126.50(18) N1 C6 Cl6 114.46(14) C5 C6 Cl6 119.01(15) C4 N41 C42 125.80(17) C4 N41 H41 117.1 C42 N41 H41 117.1 N41 C42 C44 113.04(15) N41 C42 C43 107.66(17) C44 C42 C43 111.07(18) N41 C42 H42 108.3 C44 C42 H42 108.3 C43 C42 H42 108.3 C42 C43 H431 109.5 C42 C43 H432 109.5 H431 C43 H432 109.5 C42 C43 H433 109.5 H431 C43 H433 109.5 H432 C43 H433 109.5 C49 C44 C45 118.49(19) C49 C44 C42 121.58(18) C45 C44 C42 119.89(18) C46 C45 C44 120.8(2) C46 C45 H45 119.6 C44 C45 H45 119.6 C47 C46 C45 120.5(2) C47 C46 H46 119.7 C45 C46 H46 119.7 C46 C47 C48 119.1(2) C46 C47 H47 120.4 C48 C47 H47 120.4 C49 C48 C47 120.3(2) C49 C48 H48 119.8 C47 C48 H48 119.8 C44 C49 C48 120.8(2) C44 C49 H49 119.6 C48 C49 H49 119.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C6 . 1.325(2) ? N1 C2 . 1.363(2) ? C2 N3 . 1.335(3) ? C2 N21 . 1.338(2) ? N21 H21 . .8800 ? N21 H22 . .8800 ? N3 C4 . 1.349(2) ? C4 N41 . 1.343(3) ? C4 C5 . 1.411(3) ? C5 C6 . 1.362(3) ? C5 H5 . .9500 ? C6 Cl6 . 1.7481(19) ? N41 C42 . 1.460(2) ? N41 H41 . .8800 ? C42 C44 . 1.513(3) ? C42 C43 . 1.522(3) ? C42 H42 . 1.0000 ? C43 H431 . .9800 ? C43 H432 . .9800 ? C43 H433 . .9800 ? C44 C49 . 1.378(3) ? C44 C45 . 1.386(3) ? C45 C46 . 1.380(3) ? C45 H45 . .9500 ? C46 C47 . 1.372(3) ? C46 H46 . .9500 ? C47 C48 . 1.384(3) ? C47 H47 . .9500 ? C48 C49 . 1.382(3) ? C48 H48 . .9500 ? C49 H49 . .9500 ? 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 N21 H21 N3 16_656 .88 2.23 3.098(2) 168.8 yes N21 H22 N1 13 .88 2.17 3.043(2) 171.6 yes 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 C6 N1 C2 N3 1.3(3) C6 N1 C2 N21 -177.33(17) N21 C2 N3 C4 174.25(17) N1 C2 N3 C4 -4.4(3) C2 N3 C4 N41 -175.65(16) C2 N3 C4 C5 4.3(3) N41 C4 C5 C6 178.43(18) N3 C4 C5 C6 -1.6(3) C2 N1 C6 C5 2.0(3) C2 N1 C6 Cl6 179.94(13) C4 C5 C6 N1 -1.8(3) C4 C5 C6 Cl6 -179.68(14) N3 C4 N41 C42 179.04(17) C5 C4 N41 C42 -1.0(3) C4 N41 C42 C44 -62.1(3) C4 N41 C42 C43 174.84(19) N41 C42 C44 C49 -33.2(3) C43 C42 C44 C49 88.0(2) N41 C42 C44 C45 149.19(18) C43 C42 C44 C45 -89.7(2) C49 C44 C45 C46 -.7(3) C42 C44 C45 C46 177.02(19) C44 C45 C46 C47 .1(3) C45 C46 C47 C48 .4(3) C46 C47 C48 C49 -.2(3) C45 C44 C49 C48 .9(3) C42 C44 C49 C48 -176.8(2) C47 C48 C49 C44 -.5(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105807