#======================================================================= # AUTHOR AND JOURNAL INFORMATION _publ_contact_author_name 'Katarzyna N. Jarzembska' _publ_contact_author_address ; Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland; ; _publ_contact_author_email 'katarzyna.jarzembska@gmail.com' loop_ _publ_author_name _publ_author_address 'Katarzyna N. Jarzembska' ; Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland ; 'Marcin Kubsik' ; Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland ; 'Radoslaw Kaminski' ; Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland ; 'Krzysztof Wozniak' ; Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland ; 'Paulina M. Dominiak' ; Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warszawa, Poland ; _publ_requested_journal 'Crystal Growth & Design' _publ_section_title ; From a single molecule to molecular crystal architectures - structural and energetic studies of selected uracil derivatives ; #======================================================================= data_15dmU #======================================================================= # CHEMICAL DATA _chemical_formula_moiety 'C6 H8 N2 O2' _chemical_formula_sum 'C6 H8 N2 O2' _chemical_formula_weight 140.14 #======================================================================= # CRYSTAL DATA _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1769(5) _cell_length_b 12.1325(7) _cell_length_c 7.5571(6) _cell_angle_alpha 90.0 _cell_angle_beta 91.743(7) _cell_angle_gamma 90.0 _cell_volume 657.72(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _exptl_crystal_density_diffrn 1.415 _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.108 _exptl_crystal_description unspecified _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_colour colourless _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Absorption correction done by SORTAV Blessing, R. H.: (1995) Acta Cryst. A51, 33-38 ; _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.993 #======================================================================= # EXPERIMENTAL DATA _diffrn_ambient_temperature 100(1) _diffrn_radiation_type 'Mo-K\a' _diffrn_radiation_source 'sealed tube' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Agilent Technologies KM4CCD \k-axis diffractometer' _diffrn_measurement_device_type 'Opal CCD detector' _diffrn_measurement_method '\w-scans' _diffrn_reflns_number 11143 _diffrn_reflns_theta_max 45.786 _diffrn_reflns_theta_min 3.299 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_av_r_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -15 #====================================================================== # REFINEMENT DATA _reflns_number_total 5486 _reflns_number_gt 3929 _reflns_threshold_expression 'I>2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_number_reflns 5486 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.0019P] where P=(Fo^2^+2Fc^2^)/3' /[\s^2^(Fo)] ; _refine_ls_hydrogen_treatment constr _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_extinction_method 'none' _refine_diff_density_max 0.61 _refine_diff_density_min -0.31 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' #======================================================================= # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N3 N 0.70130(6) 0.06262(3) 0.89246(5) 0.01649(7) Uani 1 1 d . . . H3 H 0.6587 -0.0017 0.9267 0.020 Uiso 1 1 calc R . . N1 N 0.93261(6) 0.16533(3) 0.75719(6) 0.01791(7) Uani 1 1 d . . . C2 C 0.86919(7) 0.06237(4) 0.80780(6) 0.01773(8) Uani 1 1 d . . . C6 C 0.83325(6) 0.25912(3) 0.79301(6) 0.01659(8) Uani 1 1 d . . . H6 H 0.8825 0.3281 0.7576 0.020 Uiso 1 1 calc R . . C4 C 0.59345(6) 0.15377(3) 0.92878(6) 0.01436(7) Uani 1 1 d . . . C5 C 0.66830(6) 0.25830(3) 0.87641(6) 0.01556(7) Uani 1 1 d . . . O2 O 0.95276(6) -0.02365(3) 0.77836(6) 0.02715(9) Uani 1 1 d . . . O4 O 0.44185(5) 0.14260(3) 1.00107(5) 0.01853(7) Uani 1 1 d . . . C8 C 0.56254(8) 0.36152(4) 0.91575(7) 0.02140(9) Uani 1 1 d . . . H8A H 0.6333 0.4257 0.8764 0.032 Uiso 1 1 calc R . . H8B H 0.5442 0.3667 1.0435 0.032 Uiso 1 1 calc R . . H8C H 0.4410 0.3596 0.8531 0.032 Uiso 1 1 calc R . . C7 C 1.11003(7) 0.17059(5) 0.66415(8) 0.02352(9) Uani 1 1 d . . . H7A H 1.1382 0.2475 0.6356 0.035 Uiso 1 1 calc R . . H7B H 1.0994 0.1275 0.5546 0.035 Uiso 1 1 calc R . . H7C H 1.2104 0.1403 0.7404 0.035 Uiso 1 1 calc R . . 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 N3 0.01844(15) 0.01050(12) 0.02063(15) 0.00092(10) 0.00239(11) 0.00087(10) N1 0.01702(15) 0.01600(14) 0.02072(16) 0.00133(11) 0.00093(12) -0.00079(11) C2 0.01867(17) 0.01413(15) 0.02042(17) 0.00025(12) 0.00107(13) 0.00171(12) C6 0.01917(17) 0.01324(14) 0.01729(16) 0.00077(12) -0.00079(12) -0.00253(12) C4 0.01774(15) 0.01074(13) 0.01455(14) 0.00020(10) -0.00029(11) 0.00035(11) C5 0.02009(16) 0.01088(13) 0.01566(15) -0.00018(11) -0.00028(12) 0.00002(11) O2 0.02794(18) 0.01743(15) 0.0365(2) 0.00007(13) 0.00771(15) 0.00817(13) O4 0.01959(14) 0.01440(13) 0.02184(15) 0.00167(10) 0.00452(11) 0.00026(10) C8 0.0293(2) 0.01386(16) 0.02109(18) -0.00075(13) 0.00210(16) 0.00312(14) C7 0.01678(17) 0.0279(2) 0.0260(2) 0.00342(17) 0.00297(15) -0.00097(16) #======================================================================= # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N3 C2 1.3813(6) . ? N3 C4 1.3821(5) . ? N3 H3 0.8800 . ? N1 C6 1.3743(6) . ? N1 C2 1.3872(6) . ? N1 C7 1.4745(6) . ? C2 O2 1.2274(6) . ? C6 C5 1.3580(6) . ? C6 H6 0.9500 . ? C4 O4 1.2396(6) . ? C4 C5 1.4375(6) . ? C5 C8 1.4988(6) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 _geom_angle_publ_flag C2 N3 C4 126.54(4) . . ? C2 N3 H3 116.7 . . ? C4 N3 H3 116.7 . . ? C6 N1 C2 120.98(4) . . ? C6 N1 C7 121.26(4) . . ? C2 N1 C7 117.76(4) . . ? O2 C2 N3 121.59(4) . . ? O2 C2 N1 123.33(4) . . ? N3 C2 N1 115.08(4) . . ? C5 C6 N1 123.38(4) . . ? C5 C6 H6 118.3 . . ? N1 C6 H6 118.3 . . ? O4 C4 N3 120.29(4) . . ? O4 C4 C5 123.92(4) . . ? N3 C4 C5 115.78(4) . . ? C6 C5 C4 118.21(4) . . ? C6 C5 C8 122.66(4) . . ? C4 C5 C8 119.13(4) . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 _geom_torsion_publ_flag C4 N3 C2 O2 -178.44(5) . . . . ? C4 N3 C2 N1 0.55(7) . . . . ? C6 N1 C2 O2 179.81(5) . . . . ? C7 N1 C2 O2 -0.29(7) . . . . ? C6 N1 C2 N3 0.84(7) . . . . ? C7 N1 C2 N3 -179.26(4) . . . . ? C2 N1 C6 C5 -0.90(7) . . . . ? C7 N1 C6 C5 179.20(4) . . . . ? C2 N3 C4 O4 177.74(4) . . . . ? C2 N3 C4 C5 -1.78(7) . . . . ? N1 C6 C5 C4 -0.42(7) . . . . ? N1 C6 C5 C8 179.48(4) . . . . ? O4 C4 C5 C6 -177.87(4) . . . . ? N3 C4 C5 C6 1.64(6) . . . . ? O4 C4 C5 C8 2.23(7) . . . . ? N3 C4 C5 C8 -178.26(4) . . . . ?