#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/00/2200079.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_2200079 loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _publ_section_title ; 2-Amino-4-chloro-6-(4-carbamoylpiperidin-1-yl)pyrimidine hemihydrate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o50 _journal_page_last o51 _journal_paper_doi 10.1107/S1600536800019589 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C10 H15 Cl N5 O, 0.5H2 O' _chemical_formula_moiety 'C10 H15 Cl N5 O, 0.5H2 O' _chemical_formula_sum 'C10 H15 Cl N5 O1.5' _chemical_formula_weight 264.72 _chemical_melting_point 480.0(10) _chemical_name_systematic ' 2-Amino-4-chloro-6-(4-carbamoylpyperidinyl)pyrimidine hemihydrate' _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 102.08(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 15.559(3) _cell_length_b 9.3139(19) _cell_length_c 16.493(3) _cell_measurement_reflns_used 5223 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 2337.2(8) _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 .994 _diffrn_measured_fraction_theta_max .994 _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 .047 _diffrn_reflns_av_sigmaI/netI .0513 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 10159 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.98 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .325 _exptl_absorpt_correction_T_max .956 _exptl_absorpt_correction_T_min .920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1112 _exptl_crystal_size_max .26 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .14 _refine_diff_density_max .235 _refine_diff_density_min -.410 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2672 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all .057 _refine_ls_R_factor_gt .041 _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^)+(0.0659P)^2^+0.5619P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .116 _reflns_number_gt 2113 _reflns_number_total 2672 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6014.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '479-481 K' was changed to '480.0(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 '479-481 K' was changed to '480.0(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 'C 2/c' _cod_database_code 2200079 _cod_database_fobs_code 2200079 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 .00203(8) .37886(15) .59398(7) .0250(3) Uani d . 1 . . N C2 -.04182(10) .27801(18) .54389(9) .0249(4) Uani d . 1 . . C N21 -.12341(9) .24368(18) .55424(9) .0296(3) Uani d . 1 . . N H21 -.1456(13) .301(3) .5787(13) .046(6) Uiso d . 1 . . H H22 -.1510(13) .186(2) .5205(12) .035(5) Uiso d . 1 . . H N3 -.01179(8) .20299(15) .48564(8) .0261(3) Uani d . 1 . . N C4 .06786(10) .24364(18) .47735(9) .0257(4) Uani d . 1 . . C Cl4 .10767(3) .14798(5) .40232(3) .03639(17) Uani d . 1 . . Cl C5 .11831(10) .34908(17) .51986(9) .0262(4) Uani d . 1 . . C H5 .1743 .3740 .5096 .033 Uiso calc R 1 . . H C6 .08140(10) .41912(17) .58057(9) .0238(3) Uani d . 1 . . C N61 .12211(8) .52898(15) .62697(8) .0268(3) Uani d . 1 . . N C62 .21122(10) .57591(18) .62698(9) .0277(4) Uani d . 1 . . C H621 .2128 .6820 .6243 .035 Uiso calc R 1 . . H H622 .2297 .5374 .5774 .035 Uiso calc R 1 . . H C63 .27461(10) .52464(18) .70472(9) .0252(3) Uani d . 1 . . C H631 .3334 .5665 .7061 .032 Uiso calc R 1 . . H H632 .2801 .4189 .7027 .032 Uiso calc R 1 . . H C64 .24399(10) .56704(18) .78406(9) .0239(3) Uani d . 1 . . C H641 .2505(11) .671(2) .7900(11) .030(5) Uiso d . 1 . . H C65 .14788(10) .52713(19) .77775(9) .0273(4) Uani d . 1 . . C H651 .1274 .5666 .8261 .034 Uiso calc R 1 . . H H652 .1422 .4213 .7789 .034 Uiso calc R 1 . . H C66 .09035(10) .5856(2) .69799(9) .0295(4) Uani d . 1 . . C H661 .0285 .5563 .6944 .037 Uiso calc R 1 . . H H662 .0929 .6918 .6980 .037 Uiso calc R 1 . . H C67 .30207(10) .50032(17) .86049(9) .0256(4) Uani d . 1 . . C O67 .26969(7) .44034(13) .91439(7) .0330(3) Uani d . 1 . . O N67 .38837(9) .50667(17) .86607(9) .0309(4) Uani d . 1 . . N H671 .4097(11) .548(2) .8278(11) .034(5) Uiso d . 1 . . H H672 .4210(12) .462(2) .9058(11) .036(5) Uiso d . 1 . . H O1W .0000 .8089(3) .2500 .0459(5) Uani d S 1 . . O H1W .0084(16) .752(3) .2890(15) .077(9) Uiso d . 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 .0209(7) .0322(8) .0218(6) .0004(6) .0046(5) .0001(6) C2 .0222(8) .0292(9) .0228(7) .0020(7) .0039(6) .0048(6) N21 .0231(8) .0367(9) .0305(8) -.0039(7) .0092(6) -.0070(7) N3 .0240(7) .0296(8) .0252(7) .0008(6) .0062(5) -.0015(6) C4 .0253(8) .0286(9) .0243(7) .0047(7) .0075(6) .0022(6) Cl4 .0337(3) .0403(3) .0387(3) .00087(18) .01579(19) -.01113(18) C5 .0230(8) .0307(9) .0263(8) .0008(7) .0081(6) .0025(6) C6 .0221(8) .0273(9) .0209(7) .0021(6) .0021(6) .0035(6) N61 .0222(7) .0322(8) .0264(6) -.0020(6) .0063(5) -.0028(6) C62 .0259(8) .0297(9) .0281(8) -.0042(7) .0073(6) .0010(7) C63 .0214(8) .0272(9) .0276(8) -.0022(7) .0064(6) -.0002(7) C64 .0225(8) .0214(9) .0275(8) .0004(6) .0046(6) -.0012(6) C65 .0237(8) .0331(9) .0264(8) .0016(7) .0081(6) -.0042(7) C66 .0233(8) .0359(10) .0286(8) .0024(7) .0040(6) -.0068(7) C67 .0255(8) .0242(9) .0274(8) .0012(6) .0060(6) -.0031(6) O67 .0288(6) .0401(7) .0314(6) .0026(5) .0092(5) .0083(5) N67 .0231(8) .0391(9) .0295(7) .0012(6) .0031(6) .0073(6) O1W .0504(13) .0568(14) .0289(10) .000 .0046(8) .000 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' O O .0106 .0060 '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 C2 N1 C6 117.27(13) N1 C2 N3 126.53(14) N1 C2 N21 117.24(14) N3 C2 N21 116.19(15) C2 N21 H21 115.2(16) C2 N21 H22 116.0(13) H21 N21 H22 124(2) C4 N3 C2 113.28(13) N3 C4 C5 127.12(15) N3 C4 Cl4 113.91(12) C5 C4 Cl4 118.97(12) C4 C5 C6 115.03(14) C4 C5 H5 122.5 C6 C5 H5 122.5 N1 C6 N61 116.91(13) N1 C6 C5 120.54(14) N61 C6 C5 122.55(14) C6 N61 C62 124.13(13) C6 N61 C66 121.95(13) C62 N61 C66 111.96(13) N61 C62 C63 110.83(12) N61 C62 H621 109.5 C63 C62 H621 109.5 N61 C62 H622 109.5 C63 C62 H622 109.5 H621 C62 H622 108.1 C62 C63 C64 112.06(13) C62 C63 H631 109.2 C64 C63 H631 109.2 C62 C63 H632 109.2 C64 C63 H632 109.2 H631 C63 H632 107.9 C67 C64 C65 111.18(13) C67 C64 C63 111.39(13) C65 C64 C63 110.76(13) C67 C64 H641 107.0(11) C65 C64 H641 109.1(10) C63 C64 H641 107.2(10) C64 C65 C66 111.20(13) C64 C65 H651 109.4 C66 C65 H651 109.4 C64 C65 H652 109.4 C66 C65 H652 109.4 H651 C65 H652 108.0 N61 C66 C65 109.03(13) N61 C66 H661 109.9 C65 C66 H661 109.9 N61 C66 H662 109.9 C65 C66 H662 109.9 H661 C66 H662 108.3 O67 C67 N67 121.74(14) O67 C67 C64 121.13(14) N67 C67 C64 117.12(14) C67 N67 H671 120.5(12) C67 N67 H672 117.7(12) H671 N67 H672 121.6(17) 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 C2 . 1.340(2) ? N1 C6 . 1.3523(19) ? C2 N3 . 1.348(2) ? C2 N21 . 1.354(2) ? N21 H21 . .79(2) ? N21 H22 . .83(2) ? N3 C4 . 1.3299(19) ? C4 C5 . 1.357(2) ? C4 Cl4 . 1.7407(16) ? C5 C6 . 1.414(2) ? C5 H5 . .95 ? C6 N61 . 1.353(2) ? N61 C62 . 1.4536(19) ? N61 C66 . 1.4617(19) ? C62 C63 . 1.522(2) ? C62 H621 . .99 ? C62 H622 . .99 ? C63 C64 . 1.535(2) ? C63 H631 . .99 ? C63 H632 . .99 ? C64 C67 . 1.521(2) ? C64 C65 . 1.523(2) ? C64 H641 . .979(19) ? C65 C66 . 1.528(2) ? C65 H651 . .99 ? C65 H652 . .99 ? C66 H661 . .99 ? C66 H662 . .99 ? C67 O67 . 1.2425(18) ? C67 N67 . 1.328(2) ? N67 H671 . .862(18) ? N67 H672 . .85(2) ? O1W H1W . .82(2) ? 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 O67 2_556 .79(2) 2.35(2) 3.049(2) 148(2) yes N21 H22 O67 8_455 .83(2) 2.25(2) 3.069(2) 170.6(19) yes N67 H671 O1W 7_566 .862(18) 2.481(19) 3.320(2) 164.6(16) yes N67 H672 N3 8_556 .85(2) 2.15(2) 2.972(2) 163.7(18) yes O1W H1W N1 5_566 .82(2) 2.32(2) 3.1171(19) 164(2) 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 6.2(2) C6 N1 C2 N21 -176.29(14) N1 C2 N3 C4 -3.7(2) N21 C2 N3 C4 178.74(14) C2 N3 C4 C5 -.5(2) C2 N3 C4 Cl4 -179.95(11) N3 C4 C5 C6 1.7(2) Cl4 C4 C5 C6 -178.88(11) C2 N1 C6 N61 174.85(14) C2 N1 C6 C5 -4.5(2) C4 C5 C6 N1 .9(2) C4 C5 C6 N61 -178.32(14) N1 C6 N61 C62 173.21(13) C5 C6 N61 C62 -7.5(2) N1 C6 N61 C66 10.5(2) C5 C6 N61 C66 -170.24(14) C6 N61 C62 C63 -103.75(17) C66 N61 C62 C63 60.50(18) N61 C62 C63 C64 -52.92(18) C62 C63 C64 C67 173.35(13) C62 C63 C64 C65 49.05(18) C67 C64 C65 C66 -176.14(13) C63 C64 C65 C66 -51.73(18) C6 N61 C66 C65 101.90(17) C62 N61 C66 C65 -62.74(18) C64 C65 C66 N61 58.02(18) C65 C64 C67 O67 -9.6(2) C63 C64 C67 O67 -133.68(15) C65 C64 C67 N67 169.11(13) C63 C64 C67 N67 45.05(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21133026