#\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2016-09-30 at 00:13:58 # Using CIFtbx version 3.0.4 1 Sep 2006 # Dictionary name : cif_core.dic # Dictionary vers : 2.4.3 # Request file : c:\nauka\wingx\files\archive.reqdat # CIF files read : new ccdc_deposit_1 yz166_hcl yz166_hcl_od #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_global #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2016-09-30 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #============================================================================== # # SUBMISSION DETAILS # Name and address of author for correspondence _publ_contact_author_name 'Justyna Kalinowska-T\/lu\'scik' _publ_contact_author_address ; Faculty of Chemistry, Jagiellonian University, R. Ingardena 3, 30-060 Krak\'ow, Poland ; _publ_contact_author_email 'kalinows@chemia.uj.edu.pl' _publ_contact_author_fax '48126340515' _publ_contact_author_phone '48126632268' _publ_contact_letter ; Submission dated :2016-09-30 Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as part of a journal submission Justyna Kalinowska-Tluscik ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; ? ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_footnote _publ_author_address ? ? ;? ; #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_new _audit_creation_date 2016-09-30T00:13:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C9 H14 N6 O' _chemical_formula_sum 'C9 H14 N6 O' _chemical_formula_weight 222.26 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _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 10.7348(5) _cell_length_b 9.1446(3) _cell_length_c 11.7753(6) _cell_angle_alpha 90 _cell_angle_beta 116.418(6) _cell_angle_gamma 90 _cell_volume 1035.22(9) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4350 _cell_measurement_theta_min 3.472 _cell_measurement_theta_max 27.771 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.426 _exptl_crystal_F_000 472 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.66181 _exptl_absorpt_correction_T_max 1 _shelx_estimated_absorpt_T_min 0.942 _shelx_estimated_absorpt_T_max 0.961 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _diffrn_ambient_temperature 130(2) _diffrn_ambient_environment N~2~ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_type Atlas _diffrn_detector_area_resol_mean 10.3756 _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_ub_11 -0.0520479 _diffrn_orient_matrix_ub_12 -0.0509204 _diffrn_orient_matrix_ub_13 -0.037122 _diffrn_orient_matrix_ub_21 -0.0503366 _diffrn_orient_matrix_ub_22 0.0411241 _diffrn_orient_matrix_ub_23 0.0099024 _diffrn_orient_matrix_ub_31 -0.0139347 _diffrn_orient_matrix_ub_32 0.0416342 _diffrn_orient_matrix_ub_33 -0.0552133 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_unetI/netI 0.0702 _diffrn_reflns_number 14724 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.948 _diffrn_reflns_theta_max 29.408 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.947 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.947 _reflns_Friedel_coverage 0 _reflns_number_total 2711 _reflns_number_gt 2101 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)' _computing_cell_refinement 'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION # #----------------------------------------------------------------------------# _atom_sites_solution_hydrogens mixed #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.4328P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.026(2) _refine_ls_number_reflns 2711 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.343 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # CONSTRAINTS AND RESTRAINTS # #----------------------------------------------------------------------------# #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O14 O 0.61396(10) 0.64649(11) 0.05427(9) 0.0238(3) Uani 1 1 d . . . . . N3 N 0.83822(13) 0.56637(14) 0.52806(11) 0.0231(3) Uani 1 1 d . . . . . N12 N 0.77897(12) 0.31170(13) 0.18324(11) 0.0169(3) Uani 1 1 d . . . . . N2 N 0.85615(13) 0.63846(13) 0.44199(11) 0.0216(3) Uani 1 1 d . . . . . N4 N 0.79869(12) 0.42535(13) 0.49023(11) 0.0201(3) Uani 1 1 d . . . . . C10 C 0.82517(14) 0.00652(15) 0.30646(14) 0.0189(3) Uani 1 1 d . . . . . H10A H 0.8378 0.0101 0.2282 0.023 Uiso 1 1 calc R U . . . H10B H 0.8897 -0.0681 0.3633 0.023 Uiso 1 1 calc R U . . . N13 N 0.67746(13) 0.40874(13) 0.09793(11) 0.0187(3) Uani 1 1 d . . . . . C6 C 0.75740(13) 0.27623(14) 0.29611(12) 0.0149(3) Uani 1 1 d . . . . . C9 C 0.67573(15) -0.03828(16) 0.27261(14) 0.0219(3) Uani 1 1 d . . . . . H9A H 0.6663 -0.0561 0.3514 0.026 Uiso 1 1 calc R U . . . H9B H 0.6535 -0.1304 0.2234 0.026 Uiso 1 1 calc R U . . . N1 N 0.82934(11) 0.54352(12) 0.34541(11) 0.0168(3) Uani 1 1 d . . . . . C8 C 0.57319(14) 0.08066(16) 0.19474(14) 0.0215(3) Uani 1 1 d . . . . . H8A H 0.4778 0.0512 0.1778 0.026 Uiso 1 1 calc R U . . . H8B H 0.5759 0.0914 0.1122 0.026 Uiso 1 1 calc R U . . . C11 C 0.86156(14) 0.15591(14) 0.37196(13) 0.0171(3) Uani 1 1 d . . . . . H11A H 0.9557 0.1847 0.3843 0.021 Uiso 1 1 calc R U . . . H11B H 0.8639 0.1476 0.4567 0.021 Uiso 1 1 calc R U . . . C14 C 0.69901(14) 0.55319(15) 0.11746(13) 0.0177(3) Uani 1 1 d . . . . . C15 C 0.83595(14) 0.59360(15) 0.22989(13) 0.0187(3) Uani 1 1 d . . . . . H15A H 0.9145 0.5459 0.222 0.022 Uiso 1 1 calc R U . . . H15B H 0.85 0.7008 0.233 0.022 Uiso 1 1 calc R U . . . C7 C 0.60819(14) 0.22761(15) 0.26439(13) 0.0182(3) Uani 1 1 d . . . . . H7A H 0.5983 0.2189 0.3438 0.022 Uiso 1 1 calc R U . . . H7B H 0.5417 0.3027 0.2107 0.022 Uiso 1 1 calc R U . . . C5 C 0.79373(13) 0.41313(15) 0.37614(13) 0.0161(3) Uani 1 1 d . . . . . H12 H 0.7799(17) 0.2320(19) 0.1392(16) 0.026(4) Uiso 1 1 d . . . . . H13 H 0.590(2) 0.377(2) 0.0480(17) 0.032(5) Uiso 1 1 d . . . . . 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 O14 0.0245(5) 0.0189(5) 0.0217(5) 0.0033(4) 0.0046(4) 0.0007(4) N3 0.0283(7) 0.0205(6) 0.0181(6) -0.0025(5) 0.0081(5) -0.0009(5) N12 0.0202(6) 0.0156(6) 0.0151(6) 0.0011(5) 0.0081(5) 0.0032(5) N2 0.0239(6) 0.0197(6) 0.0172(6) -0.0035(5) 0.0056(5) -0.0015(5) N4 0.0237(6) 0.0192(6) 0.0162(6) -0.0015(5) 0.0077(5) 0.0007(5) C10 0.0190(7) 0.0163(7) 0.0196(7) 0.0003(5) 0.0069(6) 0.0008(5) N13 0.0206(6) 0.0172(6) 0.0145(6) 0.0005(5) 0.0044(5) -0.0002(5) C6 0.0157(6) 0.0149(6) 0.0137(6) 0.0001(5) 0.0061(5) 0.0005(5) C9 0.0224(7) 0.0179(7) 0.0254(8) -0.0017(6) 0.0107(6) -0.0037(6) N1 0.0159(5) 0.0158(5) 0.0157(6) -0.0019(4) 0.0044(5) -0.0013(4) C8 0.0165(7) 0.0228(7) 0.0229(7) -0.0028(6) 0.0066(6) -0.0042(6) C11 0.0163(6) 0.0159(7) 0.0162(7) 0.0004(5) 0.0046(5) 0.0002(5) C14 0.0215(7) 0.0181(7) 0.0150(6) 0.0006(5) 0.0094(5) -0.0011(5) C15 0.0197(7) 0.0176(7) 0.0190(7) 0.0019(5) 0.0087(6) -0.0021(5) C7 0.0154(6) 0.0187(7) 0.0199(7) 0.0000(5) 0.0071(5) 0.0000(5) C5 0.0132(6) 0.0158(6) 0.0175(7) 0.0009(5) 0.0052(5) 0.0016(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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. ; 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 O14 C14 1.2291(17) . ? N3 N2 1.2933(17) . ? N3 N4 1.3686(17) . ? N12 N13 1.4178(16) . ? N12 C6 1.4829(17) . ? N12 H12 0.897(18) . ? N2 N1 1.3560(16) . ? N4 C5 1.3253(17) . ? C10 C9 1.527(2) . ? C10 C11 1.5315(18) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? N13 C14 1.3431(18) . ? N13 H13 0.902(19) . ? C6 C5 1.5101(18) . ? C6 C11 1.5395(18) . ? C6 C7 1.5396(18) . ? C9 C8 1.529(2) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? N1 C5 1.3498(17) . ? N1 C15 1.4667(17) . ? C8 C7 1.5315(19) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C14 C15 1.5226(19) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? 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 N2 N3 N4 110.97(11) . . ? N13 N12 C6 113.25(10) . . ? N13 N12 H12 107.5(11) . . ? C6 N12 H12 112.8(11) . . ? N3 N2 N1 106.31(11) . . ? C5 N4 N3 106.04(11) . . ? C9 C10 C11 111.95(11) . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C14 N13 N12 118.34(12) . . ? C14 N13 H13 118.4(12) . . ? N12 N13 H13 120.6(12) . . ? N12 C6 C5 106.14(11) . . ? N12 C6 C11 108.28(10) . . ? C5 C6 C11 108.13(10) . . ? N12 C6 C7 113.96(11) . . ? C5 C6 C7 110.05(11) . . ? C11 C6 C7 110.06(11) . . ? C10 C9 C8 110.99(11) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108 . . ? C5 N1 N2 108.69(11) . . ? C5 N1 C15 131.36(12) . . ? N2 N1 C15 119.88(11) . . ? C9 C8 C7 111.31(11) . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108 . . ? C10 C11 C6 112.87(11) . . ? C10 C11 H11A 109 . . ? C6 C11 H11A 109 . . ? C10 C11 H11B 109 . . ? C6 C11 H11B 109 . . ? H11A C11 H11B 107.8 . . ? O14 C14 N13 123.65(13) . . ? O14 C14 C15 121.84(12) . . ? N13 C14 C15 114.44(12) . . ? N1 C15 C14 107.71(10) . . ? N1 C15 H15A 110.2 . . ? C14 C15 H15A 110.2 . . ? N1 C15 H15B 110.2 . . ? C14 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? C8 C7 C6 111.36(11) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108 . . ? N4 C5 N1 107.99(12) . . ? N4 C5 C6 125.82(12) . . ? N1 C5 C6 126.18(12) . . ? 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 N4 N3 N2 N1 -0.55(15) . . . . ? N2 N3 N4 C5 0.36(15) . . . . ? C6 N12 N13 C14 87.01(14) . . . . ? N13 N12 C6 C5 -71.31(13) . . . . ? N13 N12 C6 C11 172.79(10) . . . . ? N13 N12 C6 C7 49.96(15) . . . . ? C11 C10 C9 C8 53.74(16) . . . . ? N3 N2 N1 C5 0.53(14) . . . . ? N3 N2 N1 C15 177.90(11) . . . . ? C10 C9 C8 C7 -56.16(16) . . . . ? C9 C10 C11 C6 -53.15(15) . . . . ? N12 C6 C11 C10 -71.91(14) . . . . ? C5 C6 C11 C10 173.49(11) . . . . ? C7 C6 C11 C10 53.25(15) . . . . ? N12 N13 C14 O14 -175.25(12) . . . . ? N12 N13 C14 C15 1.77(17) . . . . ? C5 N1 C15 C14 49.81(18) . . . . ? N2 N1 C15 C14 -126.87(12) . . . . ? O14 C14 C15 N1 110.87(14) . . . . ? N13 C14 C15 N1 -66.21(15) . . . . ? C9 C8 C7 C6 57.50(15) . . . . ? N12 C6 C7 C8 66.67(15) . . . . ? C5 C6 C7 C8 -174.25(11) . . . . ? C11 C6 C7 C8 -55.18(14) . . . . ? N3 N4 C5 N1 -0.01(14) . . . . ? N3 N4 C5 C6 178.86(12) . . . . ? N2 N1 C5 N4 -0.32(14) . . . . ? C15 N1 C5 N4 -177.28(12) . . . . ? N2 N1 C5 C6 -179.18(12) . . . . ? C15 N1 C5 C6 3.9(2) . . . . ? N12 C6 C5 N4 -174.62(12) . . . . ? C11 C6 C5 N4 -58.63(17) . . . . ? C7 C6 C5 N4 61.62(17) . . . . ? N12 C6 C5 N1 4.05(17) . . . . ? C11 C6 C5 N1 120.04(14) . . . . ? C7 C6 C5 N1 -119.71(14) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF