#------------------------------------------------------------------------------ #$Date: 2020-05-08 09:18:41 +0100 (Fri, 08 May 2020) $ #$Revision: 251907 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500106.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500106 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _journal_name_full 'Personal communication to COD' _journal_year 2020 _chemical_formula_moiety 'C6 H7 Cl N2 O2' _chemical_formula_sum 'C6 H7 Cl N2 O2' _chemical_formula_weight 174.59 _chemical_name_common 4-chloro-2,6-dimethoxypyrimidine _chemical_name_systematic 4-chloro-2,6-dimethoxypyrimidine _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-05-07 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.2140(6) _cell_length_b 6.5266(3) _cell_length_c 8.6159(4) _cell_measurement_reflns_used 9912 _cell_measurement_temperature 105 _cell_measurement_theta_max 60.631 _cell_measurement_theta_min 5.334 _cell_volume 743.06(6) _computing_cell_refinement ; SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 105 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_detector_type 'Bruker Photon 100 CMOS Detector' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0209 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 13293 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.707 _diffrn_reflns_theta_min 5.332 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.1998568 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.88 _exptl_absorpt_coefficient_mu 2.754 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.5639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1298 before and 0.0546 after correction. The Ratio of minimum to maximum transmission is 0.7500. The \l/2 correction factor is 0.00150. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.561 _exptl_crystal_description Block _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. ; _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _refine_diff_density_max 0.459 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.072 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 69 _refine_ls_number_reflns 928 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.149 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0262 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.2360P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.0720 _refine_special_details ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5) H6A(0.5) H6B(0.5) H6C(0.5) 3.a Aromatic/amide H refined with riding coordinates: C2(H2) 3.b Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C6(H6A,H6B,H6C) ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 905 _reflns_number_total 928 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file meocln.cif _cod_data_source_block meocln _cod_database_code 3500106 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z' 4 'x+1/2, -y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z' 8 '-x-1/2, y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.62411(3) 0.750000 0.57472(4) 0.01849(14) Uani 1 2 d S T P . . O1 O 0.49370(8) 0.750000 0.02714(12) 0.0195(2) Uani 1 2 d S T P . . O2 O 0.26686(8) 0.750000 0.42252(11) 0.0185(3) Uani 1 2 d S T P . . N1 N 0.43488(9) 0.750000 0.49009(13) 0.0148(3) Uani 1 2 d S T P . . N2 N 0.37705(8) 0.750000 0.22613(15) 0.0151(3) Uani 1 2 d S T P . . C1 C 0.52928(11) 0.750000 0.43464(16) 0.0145(3) Uani 1 2 d S T P . . C2 C 0.55573(11) 0.750000 0.28100(17) 0.0167(3) Uani 1 2 d S T P . . H2 H 0.623970 0.750000 0.246312 0.020 Uiso 1 2 calc R U P . . C3 C 0.47259(11) 0.750000 0.17940(16) 0.0152(3) Uani 1 2 d S T P . . C4 C 0.36441(10) 0.750000 0.38051(17) 0.0145(3) Uani 1 2 d S T P . . C5 C 0.40884(13) 0.750000 -0.07877(16) 0.0204(3) Uani 1 2 d S T P . . H5A H 0.372192 0.880006 -0.069778 0.031 Uiso 0.5 1 calc R U P A -1 H5B H 0.363295 0.636470 -0.053011 0.031 Uiso 0.5 1 calc R U P A -1 H5C H 0.433495 0.733524 -0.185312 0.031 Uiso 0.5 1 calc R U P A -1 C6 C 0.24529(12) 0.750000 0.58663(17) 0.0227(4) Uani 1 2 d S T P . . H6A H 0.280093 0.634584 0.636072 0.034 Uiso 0.5 1 calc R U P B -1 H6B H 0.172162 0.736713 0.602697 0.034 Uiso 0.5 1 calc R U P B -1 H6C H 0.268951 0.878703 0.632626 0.034 Uiso 0.5 1 calc R U P B -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0172(2) 0.0191(2) 0.0192(2) 0.000 -0.00666(11) 0.000 O1 0.0182(5) 0.0275(6) 0.0129(5) 0.000 0.0007(4) 0.000 O2 0.0133(5) 0.0290(6) 0.0131(5) 0.000 0.0000(3) 0.000 N1 0.0159(6) 0.0149(6) 0.0135(5) 0.000 -0.0011(4) 0.000 N2 0.0160(6) 0.0166(6) 0.0127(6) 0.000 -0.0006(4) 0.000 C1 0.0154(7) 0.0120(6) 0.0161(7) 0.000 -0.0037(5) 0.000 C2 0.0145(6) 0.0182(7) 0.0172(6) 0.000 0.0002(5) 0.000 C3 0.0180(6) 0.0137(6) 0.0138(6) 0.000 0.0007(5) 0.000 C4 0.0151(7) 0.0134(6) 0.0151(7) 0.000 -0.0002(5) 0.000 C5 0.0214(8) 0.0270(8) 0.0128(7) 0.000 -0.0018(5) 0.000 C6 0.0179(7) 0.0360(10) 0.0140(7) 0.000 0.0025(5) 0.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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' Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0387 0.0241 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C3 O1 C5 117.13(11) . . C4 O2 C6 117.08(12) . . C4 N1 C1 113.65(12) . . C3 N2 C4 114.85(12) . . N1 C1 Cl1 115.12(10) . . N1 C1 C2 125.74(13) . . C2 C1 Cl1 119.14(12) . . C1 C2 H2 123.1 . . C1 C2 C3 113.76(13) . . C3 C2 H2 123.1 . . O1 C3 C2 116.54(13) . . N2 C3 O1 119.69(13) . . N2 C3 C2 123.77(13) . . O2 C4 N2 112.84(12) . . N1 C4 O2 118.92(13) . . N1 C4 N2 128.24(13) . . O1 C5 H5A 109.5 . . O1 C5 H5B 109.5 . . O1 C5 H5C 109.5 . . H5A C5 H5B 109.5 . . H5A C5 H5C 109.5 . . H5B C5 H5C 109.5 . . O2 C6 H6A 109.5 . . O2 C6 H6B 109.5 . . O2 C6 H6C 109.5 . . H6A C6 H6B 109.5 . . H6A C6 H6C 109.5 . . H6B C6 H6C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl1 C1 1.7398(14) . O1 C3 1.3412(16) . O1 C5 1.4457(18) . O2 C4 1.3389(17) . O2 C6 1.4424(17) . N1 C1 1.3358(19) . N1 C4 1.3260(18) . N2 C3 1.3250(18) . N2 C4 1.3406(19) . C1 C2 1.3692(19) . C2 H2 0.9500 . C2 C3 1.4047(19) . C5 H5A 0.9800 . C5 H5B 0.9800 . C5 H5C 0.9800 . C6 H6A 0.9800 . C6 H6B 0.9800 . C6 H6C 0.9800 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C2 H2 O2 0.95 2.38 3.2952(18) 160.7 6_656 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Cl1 C1 C2 C3 180.000(0) . . . . N1 C1 C2 C3 0.000(0) . . . . C1 N1 C4 O2 180.000(0) . . . . C1 N1 C4 N2 0.000(0) . . . . C1 C2 C3 O1 180.000(0) . . . . C1 C2 C3 N2 0.000(0) . . . . C3 N2 C4 O2 180.0 . . . . C3 N2 C4 N1 0.000(0) . . . . C4 N1 C1 Cl1 180.0 . . . . C4 N1 C1 C2 0.000(0) . . . . C4 N2 C3 O1 180.0 . . . . C4 N2 C3 C2 0.000(0) . . . . C5 O1 C3 N2 0.000(0) . . . . C5 O1 C3 C2 180.0 . . . . C6 O2 C4 N1 0.000(0) . . . . C6 O2 C4 N2 180.000(0) . . . . _cod_database_fobs_code 3500106