#\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2016-06-10 at 10:42:08 # Using CIFtbx version 3.0.4 1 Sep 2006 # Dictionary name : cif_core.dic # Dictionary vers : 2.4.3 # Request file : c:\wingx\files\archive.reqdat # CIF files read : php628_2 #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_global #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2016-06-10 _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 'Kurpiewska, Katarzyna' _publ_contact_author_address ; Faculty of Chemistry, Jagiellonian University R. Ingardena 3, 30-060 Krakow ; _publ_contact_author_email 'kurpiews@chemia.uj.edu.pl' _publ_contact_author_fax '48126340515' _publ_contact_author_phone '48126632921' _publ_contact_letter ; Submission dated :2016-06-10 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 a personal communication This CIF is submitted as part of a journal submission ; #============================================================================== # # 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_php628_2 _audit_creation_date 2016-06-10T10:42:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C18 H22 N6 O3' _chemical_formula_moiety 'C18 H22 N6 O3' _chemical_formula_weight 370.42 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_cell_setting monoclinic 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 9.5857(2) _cell_length_b 14.8105(2) _cell_length_c 13.4801(2) _cell_angle_alpha 90 _cell_angle_beta 110.159(2) _cell_angle_gamma 90 _cell_volume 1796.52(5) _cell_formula_units_Z 4 _cell_measurement_temperature 122.1(3) _cell_measurement_reflns_used 17769 _cell_measurement_theta_min 2.9812 _cell_measurement_theta_max 76.6338 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.37 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.798 _exptl_absorpt_correction_T_min 0.44361 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 122.1(3) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator 'mirror' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_detector_area_resol_mean 10.3756 _diffrn_reflns_number 32027 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.9812 _diffrn_reflns_theta_max 76.6338 _diffrn_measured_fraction_theta_max 0.9948 _diffrn_reflns_theta_full 74.3338 _diffrn_measured_fraction_theta_full 0.9992 _reflns_number_total 3769 _reflns_number_gt 3349 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION # #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc ' _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 0.0017(4) _refine_ls_number_reflns 3791 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.307 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # 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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O19 O 0.43726(10) 0.60338(6) 0.12540(7) 0.0296(2) Uani 1 d . . . O20 O 0.61975(10) 0.59147(6) 0.05471(6) 0.0285(2) Uani 1 d . . . O10 O 0.40041(10) 1.07420(5) -0.10352(7) 0.0312(2) Uani 1 d . . . N17 N 0.46143(11) 0.70765(6) 0.00839(7) 0.0256(2) Uani 1 d . . . N11 N 0.37537(11) 0.92334(6) -0.11291(7) 0.0246(2) Uani 1 d . . . N5 N 0.15661(11) 0.93243(6) -0.30357(7) 0.0247(2) Uani 1 d . . . N2 N 0.12149(11) 0.78873(7) -0.33018(8) 0.0295(2) Uani 1 d . . . N3 N 0.02731(12) 0.83624(8) -0.41341(8) 0.0331(2) Uani 1 d . . . N4 N 0.04686(12) 0.92259(7) -0.39850(8) 0.0318(2) Uani 1 d . . . C14 C 0.34431(13) 0.76483(8) 0.02077(9) 0.0258(2) Uani 1 d . . . H14A H 0.3878 0.8188 0.06 0.031 Uiso 1 calc R . . H14B H 0.2924 0.7326 0.0602 0.031 Uiso 1 calc R . . C13 C 0.23557(12) 0.79090(8) -0.08702(9) 0.0252(2) Uani 1 d . . . H13A H 0.1627 0.8325 -0.078 0.03 Uiso 1 calc R . . H13B H 0.1833 0.7374 -0.1222 0.03 Uiso 1 calc R . . C8 C 0.08524(14) 1.07253(8) -0.23759(10) 0.0313(3) Uani 1 d . . . H8A H 0.0068 1.0834 -0.3036 0.047 Uiso 1 calc R . . H8B H 0.1219 1.1291 -0.204 0.047 Uiso 1 calc R . . H8C H 0.0478 1.0372 -0.1925 0.047 Uiso 1 calc R . . C15 C 0.43968(13) 0.77334(8) -0.16338(9) 0.0252(2) Uani 1 d . . . H15A H 0.3968 0.7193 -0.2026 0.03 Uiso 1 calc R . . H15B H 0.4953 0.8042 -0.2013 0.03 Uiso 1 calc R . . C18 C 0.50044(13) 0.63269(7) 0.06775(8) 0.0242(2) Uani 1 d . . . C1 C 0.20012(13) 0.85068(8) -0.26386(8) 0.0242(2) Uani 1 d . . . C9 C 0.33773(12) 1.00645(7) -0.15178(8) 0.0241(2) Uani 1 d . . . C6 C 0.21149(12) 1.02132(7) -0.25782(8) 0.0238(2) Uani 1 d . . . C16 C 0.54516(13) 0.74679(8) -0.05375(9) 0.0251(2) Uani 1 d . . . H16A H 0.6169 0.7032 -0.0604 0.03 Uiso 1 calc R . . H16B H 0.5989 0.7996 -0.0178 0.03 Uiso 1 calc R . . C12 C 0.31395(12) 0.83546(7) -0.15710(8) 0.0225(2) Uani 1 d . . . C7 C 0.27079(14) 1.07378(8) -0.33234(9) 0.0290(3) Uani 1 d . . . H7A H 0.3489 1.0399 -0.3443 0.044 Uiso 1 calc R . . H7B H 0.3089 1.131 -0.3012 0.044 Uiso 1 calc R . . H7C H 0.1919 1.0834 -0.3984 0.044 Uiso 1 calc R . . C22 C 0.74686(13) 0.55606(8) 0.24109(9) 0.0276(2) Uani 1 d . . . C26 C 0.80542(17) 0.53367(10) 0.42806(11) 0.0402(3) Uani 1 d . . . H26 H 0.8069 0.4964 0.484 0.048 Uiso 1 calc R . . C27 C 0.74679(16) 0.50185(9) 0.32537(10) 0.0349(3) Uani 1 d . . . H27 H 0.7072 0.4439 0.3127 0.042 Uiso 1 calc R . . C23 C 0.80502(14) 0.64283(8) 0.26162(10) 0.0298(3) Uani 1 d . . . H23 H 0.8068 0.6795 0.2061 0.036 Uiso 1 calc R . . C25 C 0.86196(15) 0.62057(10) 0.44822(10) 0.0358(3) Uani 1 d . . . H25 H 0.9005 0.6419 0.5172 0.043 Uiso 1 calc R . . C21 C 0.68388(15) 0.52051(8) 0.12958(9) 0.0314(3) Uani 1 d . . . H21A H 0.7623 0.4912 0.1113 0.038 Uiso 1 calc R . . H21B H 0.6083 0.4757 0.1255 0.038 Uiso 1 calc R . . C24 C 0.86046(13) 0.67512(9) 0.36457(10) 0.0319(3) Uani 1 d . . . H24 H 0.8968 0.7338 0.3774 0.038 Uiso 1 calc R . . H11 H 0.448(2) 0.9236(11) -0.0495(14) 0.042(4) Uiso 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 O19 0.0353(5) 0.0273(4) 0.0280(4) 0.0049(3) 0.0132(4) 0.0000(3) O20 0.0342(4) 0.0278(4) 0.0239(4) 0.0036(3) 0.0104(3) 0.0082(3) O10 0.0366(5) 0.0226(4) 0.0264(4) 0.0003(3) 0.0007(3) -0.0045(3) N17 0.0285(5) 0.0256(5) 0.0263(5) 0.0052(4) 0.0140(4) 0.0044(4) N11 0.0273(5) 0.0221(5) 0.0196(5) -0.0001(3) 0.0020(4) -0.0018(4) N5 0.0262(5) 0.0264(5) 0.0182(4) 0.0001(3) 0.0033(4) -0.0003(4) N2 0.0307(5) 0.0305(5) 0.0245(5) -0.0046(4) 0.0059(4) -0.0025(4) N3 0.0348(6) 0.0348(6) 0.0245(5) -0.0041(4) 0.0034(4) -0.0021(4) N4 0.0328(5) 0.0355(5) 0.0207(5) -0.0017(4) 0.0010(4) -0.0018(4) C14 0.0293(6) 0.0257(5) 0.0257(5) 0.0026(4) 0.0135(5) 0.0030(4) C13 0.0255(5) 0.0245(5) 0.0267(6) 0.0002(4) 0.0104(4) -0.0008(4) C8 0.0287(6) 0.0322(6) 0.0321(6) -0.0036(5) 0.0090(5) 0.0025(5) C15 0.0294(6) 0.0249(5) 0.0232(5) 0.0010(4) 0.0118(4) 0.0022(4) C18 0.0285(5) 0.0228(5) 0.0198(5) -0.0016(4) 0.0063(4) -0.0004(4) C1 0.0255(5) 0.0248(5) 0.0216(5) -0.0017(4) 0.0074(4) -0.0009(4) C9 0.0266(5) 0.0234(5) 0.0209(5) 0.0006(4) 0.0065(4) -0.0017(4) C6 0.0268(5) 0.0226(5) 0.0197(5) 0.0007(4) 0.0053(4) 0.0006(4) C16 0.0261(5) 0.0263(5) 0.0253(5) 0.0030(4) 0.0118(4) 0.0023(4) C12 0.0255(5) 0.0205(5) 0.0204(5) -0.0013(4) 0.0064(4) -0.0012(4) C7 0.0371(6) 0.0257(5) 0.0245(6) 0.0040(4) 0.0109(5) 0.0012(5) C22 0.0278(5) 0.0272(5) 0.0277(6) 0.0031(4) 0.0096(4) 0.0056(4) C26 0.0493(8) 0.0444(7) 0.0293(6) 0.0092(5) 0.0164(6) 0.0032(6) C27 0.0429(7) 0.0298(6) 0.0331(6) 0.0052(5) 0.0146(5) 0.0004(5) C23 0.0290(6) 0.0298(6) 0.0298(6) 0.0050(5) 0.0093(5) 0.0024(4) C25 0.0335(6) 0.0460(7) 0.0269(6) -0.0016(5) 0.0090(5) 0.0048(5) C21 0.0378(6) 0.0252(6) 0.0283(6) 0.0031(4) 0.0076(5) 0.0075(5) C24 0.0254(6) 0.0322(6) 0.0354(6) -0.0017(5) 0.0071(5) 0.0013(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 O19 C18 1.2180(14) . ? O20 C18 1.3602(14) . ? O20 C21 1.4400(14) . ? O10 C9 1.2335(14) . ? N17 C18 1.3440(14) . ? N17 C14 1.4610(14) . ? N17 C16 1.4646(14) . ? N11 C9 1.3378(14) . ? N11 C12 1.4676(13) . ? N5 C1 1.3314(14) . ? N5 N4 1.3557(13) . ? N5 C6 1.4720(14) . ? N2 C1 1.3209(14) . ? N2 N3 1.3678(15) . ? N3 N4 1.2980(15) . ? C14 C13 1.5176(15) . ? C13 C12 1.5432(15) . ? C8 C6 1.5303(16) . ? C15 C16 1.5268(15) . ? C15 C12 1.5415(15) . ? C1 C12 1.4934(15) . ? C9 C6 1.5374(15) . ? C6 C7 1.5263(15) . ? C22 C27 1.3913(17) . ? C22 C23 1.3902(17) . ? C22 C21 1.5085(17) . ? C26 C27 1.385(2) . ? C26 C25 1.387(2) . ? C23 C24 1.3888(18) . ? C25 C24 1.3833(19) . ? 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 C18 O20 C21 114.32(9) . . ? C18 N17 C14 118.55(9) . . ? C18 N17 C16 124.92(9) . . ? C14 N17 C16 115.47(9) . . ? C9 N11 C12 129.85(9) . . ? C1 N5 N4 108.38(9) . . ? C1 N5 C6 128.88(9) . . ? N4 N5 C6 122.73(9) . . ? C1 N2 N3 105.02(10) . . ? N4 N3 N2 111.14(10) . . ? N3 N4 N5 106.01(10) . . ? N17 C14 C13 109.84(9) . . ? C14 C13 C12 112.11(9) . . ? C16 C15 C12 111.72(9) . . ? O19 C18 N17 125.22(11) . . ? O19 C18 O20 123.21(10) . . ? N17 C18 O20 111.57(9) . . ? N2 C1 N5 109.45(10) . . ? N2 C1 C12 127.19(10) . . ? N5 C1 C12 123.25(10) . . ? O10 C9 N11 121.69(10) . . ? O10 C9 C6 117.26(10) . . ? N11 C9 C6 121.04(9) . . ? N5 C6 C7 109.87(9) . . ? N5 C6 C8 109.12(9) . . ? C7 C6 C8 111.21(9) . . ? N5 C6 C9 108.33(8) . . ? C7 C6 C9 109.42(9) . . ? C8 C6 C9 108.83(9) . . ? N17 C16 C15 110.18(9) . . ? N11 C12 C1 108.36(9) . . ? N11 C12 C13 110.04(9) . . ? C1 C12 C13 107.84(9) . . ? N11 C12 C15 109.85(9) . . ? C1 C12 C15 111.26(9) . . ? C13 C12 C15 109.46(9) . . ? C27 C22 C23 118.93(11) . . ? C27 C22 C21 119.98(11) . . ? C23 C22 C21 121.09(11) . . ? C27 C26 C25 120.55(12) . . ? C26 C27 C22 120.38(12) . . ? C24 C23 C22 120.43(11) . . ? C26 C25 C24 119.27(12) . . ? O20 C21 C22 111.80(9) . . ? C23 C24 C25 120.42(12) . . ? # 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