# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 881646' #TrackingRef 'Combined.cif' #============================================================================== _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; _cell_length_a 11.4072(9) _cell_length_b 10.0831(4) _cell_length_c 10.6740(9) _cell_angle_alpha 90 _cell_angle_beta 117.075(11) _cell_angle_gamma 90 _cell_volume 1093.17(17) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C20 H28 N12 # Dc = 1.33 Fooo = 464.00 Mu = 7.12 M = 218.26 # Found Formula = C20 H28 N12 # Dc = 1.33 FOOO = 464.00 Mu = 7.12 M = 218.26 _chemical_formula_sum 'C20 H28 N12' _chemical_formula_moiety 'C20 H28 N12' _chemical_compound_source synthesized _chemical_formula_weight 436.52 _cell_measurement_reflns_used 5555 _cell_measurement_theta_min 4.3523 _cell_measurement_theta_max 76.6679 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.08 _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.712 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_T_min 0.64918 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrysAlis Pro, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis Pro, (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlis Pro, (Oxford Diffraction, 2010)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 150 _diffrn_reflns_number 11188 _reflns_number_total 2296 _diffrn_reflns_av_R_equivalents 0.0823 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2296 # Theoretical number of reflections is about 3800 _diffrn_reflns_theta_min 4.353 _diffrn_reflns_theta_max 76.795 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 75.259 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -14 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 2.18 _oxford_diffrn_Wilson_scale 0.01 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.33 _refine_diff_density_max 0.36 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 1835 _refine_ls_number_restraints 0 _refine_ls_number_parameters 146 _oxford_refine_ls_R_factor_ref 0.0876 _refine_ls_wR_factor_ref 0.2574 _refine_ls_goodness_of_fit_ref 1.0816 _refine_ls_shift/su_max 0.0001504 _refine_ls_shift/su_mean 0.0000167 # The values computed from all data _oxford_reflns_number_all 1835 _refine_ls_R_factor_all 0.0876 _refine_ls_wR_factor_all 0.2574 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1648 _refine_ls_R_factor_gt 0.0830 _refine_ls_wR_factor_gt 0.2523 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.18P)^2^ + 1.08P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.6632(3) 1.0949(3) 0.8876(3) 0.0267 1.0000 Uani . . . . . . N2 N 0.5390(3) 1.0571(3) 0.8042(4) 0.0342 1.0000 Uani . . . . . . N3 N 0.5453(3) 0.9476(3) 0.7397(4) 0.0345 1.0000 Uani . . . . . . C4 C 0.6729(4) 0.9152(3) 0.7822(4) 0.0239 1.0000 Uani . . . . . . C5 C 0.7493(3) 1.0094(4) 0.8772(3) 0.0265 1.0000 Uani . . . . . . C6 C 0.7112(4) 0.7975(3) 0.7244(4) 0.0295 1.0000 Uani . . . . . . C7 C 0.6875(4) 0.8207(4) 0.5735(4) 0.0300 1.0000 Uani . . . . . . C8 C 0.7734(4) 0.9284(4) 0.5579(4) 0.0329 1.0000 Uani . . . . . . C9 C 0.9153(4) 0.8935(3) 0.6208(4) 0.0273 1.0000 Uani . . . . . . N10 N 0.9597(3) 0.7755(3) 0.5956(4) 0.0413 1.0000 Uani . . . . . . N11 N 1.0882(4) 0.7747(3) 0.6599(4) 0.0414 1.0000 Uani . . . . . . N12 N 1.1285(3) 0.8910(3) 0.7281(3) 0.0281 1.0000 Uani . . . . . . C13 C 1.0235(4) 0.9671(3) 0.7067(4) 0.0290 1.0000 Uani . . . . . . C14 C 1.2687(4) 0.9221(4) 0.8048(4) 0.0310 1.0000 Uani . . . . . . C15 C 1.3475(4) 0.8129(4) 0.9038(4) 0.0300 1.0000 Uani . . . . . . C16 C 1.3133(4) 0.7870(3) 1.0238(4) 0.0277 1.0000 Uani . . . . . . H51 H 0.8407 1.0124 0.9250 0.0356 1.0000 Uiso R . . . . . H62 H 0.8034 0.7780 0.7850 0.0375 1.0000 Uiso R . . . . . H61 H 0.6579 0.7220 0.7259 0.0385 1.0000 Uiso R . . . . . H71 H 0.5963 0.8477 0.5206 0.0380 1.0000 Uiso R . . . . . H72 H 0.7015 0.7379 0.5337 0.0385 1.0000 Uiso R . . . . . H81 H 0.7656 1.0087 0.6036 0.0416 1.0000 Uiso R . . . . . H82 H 0.7444 0.9452 0.4577 0.0406 1.0000 Uiso R . . . . . H131 H 1.0239 1.0525 0.7431 0.0364 1.0000 Uiso R . . . . . H142 H 1.2769 1.0026 0.8594 0.0387 1.0000 Uiso R . . . . . H141 H 1.3003 0.9397 0.7355 0.0391 1.0000 Uiso R . . . . . H151 H 1.4410 0.8361 0.9444 0.0384 1.0000 Uiso R . . . . . H152 H 1.3339 0.7326 0.8494 0.0382 1.0000 Uiso R . . . . . H161 H 1.3673 0.7146 1.0826 0.0368 1.0000 Uiso R . . . . . H162 H 1.2209 0.7626 0.9885 0.0359 1.0000 Uiso 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 N1 0.0289(16) 0.0210(15) 0.0315(15) -0.0002(11) 0.0149(12) -0.0009(12) N2 0.0267(17) 0.0269(17) 0.0466(18) -0.0109(14) 0.0145(14) -0.0033(13) N3 0.0286(17) 0.0276(17) 0.0455(18) -0.0115(14) 0.0153(14) -0.0041(13) C4 0.0293(18) 0.0144(15) 0.0303(16) 0.0000(13) 0.0156(14) -0.0010(13) C5 0.0264(18) 0.0235(17) 0.0313(17) -0.0010(14) 0.0148(14) -0.0002(14) C6 0.036(2) 0.0174(17) 0.0387(19) 0.0004(14) 0.0203(16) 0.0008(14) C7 0.0298(19) 0.0253(19) 0.0332(18) -0.0051(14) 0.0128(15) 0.0001(15) C8 0.036(2) 0.0291(19) 0.0357(19) 0.0075(15) 0.0179(16) 0.0085(16) C9 0.037(2) 0.0190(17) 0.0300(17) 0.0019(13) 0.0193(16) 0.0025(14) N10 0.0381(19) 0.0265(19) 0.055(2) -0.0120(14) 0.0175(16) 0.0030(14) N11 0.039(2) 0.0262(19) 0.057(2) -0.0131(15) 0.0194(16) -0.0002(14) N12 0.0352(17) 0.0173(15) 0.0340(16) -0.0012(11) 0.0178(13) -0.0001(12) C13 0.039(2) 0.0150(16) 0.0351(18) 0.0006(13) 0.0193(16) 0.0027(14) C14 0.034(2) 0.0270(19) 0.0326(18) 0.0006(14) 0.0162(16) -0.0059(15) C15 0.035(2) 0.0249(18) 0.0344(18) -0.0015(14) 0.0190(16) 0.0032(15) C16 0.036(2) 0.0145(17) 0.0326(17) -0.0026(13) 0.0156(15) -0.0024(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 9.4(14) loop_ _oxford_twin_element_scale_factors 0.743(6) 0.257(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C16 2_777 1.468(4) yes N1 . N2 . 1.340(4) yes N1 . C5 . 1.349(5) yes N2 . N3 . 1.320(4) yes N3 . C4 . 1.353(5) yes C4 . C5 . 1.373(5) yes C4 . C6 . 1.491(5) yes C5 . H51 . 0.930 no C6 . C7 . 1.525(5) yes C6 . H62 . 0.972 no C6 . H61 . 0.979 no C7 . C8 . 1.522(5) yes C7 . H71 . 0.970 no C7 . H72 . 0.982 no C8 . C9 . 1.485(5) yes C8 . H81 . 0.970 no C8 . H82 . 0.980 no C9 . N10 . 1.367(5) yes C9 . C13 . 1.373(5) yes N10 . N11 . 1.305(5) yes N11 . N12 . 1.345(4) yes N12 . C13 . 1.352(5) yes N12 . C14 . 1.460(5) yes C13 . H131 . 0.944 no C14 . C15 . 1.508(5) yes C14 . H142 . 0.978 no C14 . H141 . 0.975 no C15 . C16 . 1.521(5) yes C15 . H151 . 0.979 no C15 . H152 . 0.968 no C16 . H161 . 0.977 no C16 . H162 . 0.976 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C16 2_777 N1 . N2 . 119.1(3) yes C16 2_777 N1 . C5 . 130.2(3) yes N2 . N1 . C5 . 110.7(3) yes N1 . N2 . N3 . 107.0(3) yes N2 . N3 . C4 . 109.4(3) yes N3 . C4 . C5 . 107.7(3) yes N3 . C4 . C6 . 121.8(3) yes C5 . C4 . C6 . 130.5(3) yes C4 . C5 . N1 . 105.2(3) yes C4 . C5 . H51 . 127.2 no N1 . C5 . H51 . 127.7 no C4 . C6 . C7 . 111.8(3) yes C4 . C6 . H62 . 108.6 no C7 . C6 . H62 . 110.6 no C4 . C6 . H61 . 108.1 no C7 . C6 . H61 . 108.9 no H62 . C6 . H61 . 108.9 no C6 . C7 . C8 . 114.3(3) yes C6 . C7 . H71 . 106.5 no C8 . C7 . H71 . 108.1 no C6 . C7 . H72 . 109.9 no C8 . C7 . H72 . 108.7 no H71 . C7 . H72 . 109.2 no C7 . C8 . C9 . 113.9(3) yes C7 . C8 . H81 . 109.3 no C9 . C8 . H81 . 107.6 no C7 . C8 . H82 . 109.1 no C9 . C8 . H82 . 107.0 no H81 . C8 . H82 . 110.0 no C8 . C9 . N10 . 122.9(3) yes C8 . C9 . C13 . 129.6(3) yes N10 . C9 . C13 . 107.6(3) yes C9 . N10 . N11 . 109.2(3) yes N10 . N11 . N12 . 107.8(3) yes N11 . N12 . C13 . 110.2(3) yes N11 . N12 . C14 . 120.5(3) yes C13 . N12 . C14 . 129.2(3) yes C9 . C13 . N12 . 105.3(3) yes C9 . C13 . H131 . 127.1 no N12 . C13 . H131 . 127.6 no N12 . C14 . C15 . 112.8(3) yes N12 . C14 . H142 . 107.2 no C15 . C14 . H142 . 108.9 no N12 . C14 . H141 . 107.6 no C15 . C14 . H141 . 110.8 no H142 . C14 . H141 . 109.5 no C14 . C15 . C16 . 114.6(3) yes C14 . C15 . H151 . 108.5 no C16 . C15 . H151 . 108.3 no C14 . C15 . H152 . 108.0 no C16 . C15 . H152 . 109.2 no H151 . C15 . H152 . 108.0 no C15 . C16 . N1 2_777 111.2(3) yes C15 . C16 . H161 . 110.0 no N1 2_777 C16 . H161 . 108.4 no C15 . C16 . H162 . 111.4 no N1 2_777 C16 . H162 . 107.5 no H161 . C16 . H162 . 108.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C16 . H161 . N3 4_665 169.02(11) 0.977 2.551 3.515(6) yes data_2DMSOCH2CL2 _database_code_depnum_ccdc_archive 'CCDC 881647' #TrackingRef 'Combined.cif' #============================================================================== _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 5.5624(2) _cell_length_b 9.4120(3) _cell_length_c 12.0631(5) _cell_angle_alpha 76.0194(16) _cell_angle_beta 86.5052(15) _cell_angle_gamma 81.839(2) _cell_volume 606.40(4) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C26 N12 # Dc = 1.32 Fooo = 264.00 Mu = 0.88 M = 240.18 # Found Formula = C26 H24 N12 # Dc = 1.38 FOOO = 264.00 Mu = 0.91 M = 252.28 _chemical_formula_sum 'C26 H24 N12' _chemical_formula_moiety 'C26 H24 N12' _chemical_compound_source synthesized _chemical_formula_weight 504.56 _cell_measurement_reflns_used 2513 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.050 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_max 0.160 _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.091 # Sheldrick geometric approximatio 0.99 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 9190 _reflns_number_total 2750 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2750 # Theoretical number of reflections is about 4352 _diffrn_reflns_theta_min 5.156 _diffrn_reflns_theta_max 27.503 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.127 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min -11 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 1.71 _oxford_diffrn_Wilson_scale 2.58 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.41 _refine_diff_density_max 0.38 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2158 _refine_ls_number_restraints 0 _refine_ls_number_parameters 172 _oxford_refine_ls_R_factor_ref 0.0692 _refine_ls_wR_factor_ref 0.1475 _refine_ls_goodness_of_fit_ref 0.9471 _refine_ls_shift/su_max 0.0001927 _refine_ls_shift/su_mean 0.0000158 # The values computed from all data _oxford_reflns_number_all 2158 _refine_ls_R_factor_all 0.0692 _refine_ls_wR_factor_all 0.1475 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1611 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_gt 0.1185 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 21.7 35.1 21.2 9.06 2.04 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.9156(3) 0.2153(2) 0.36787(16) 0.0297 1.0000 Uani . . . . . . . N2 N 0.6939(3) 0.1976(2) 0.33932(15) 0.0231 1.0000 Uani . . . . . . . C3 C 0.6468(4) 0.1964(2) 0.22114(17) 0.0249 1.0000 Uani . . . . . . . C4 C 0.4199(4) 0.3011(2) 0.17816(18) 0.0244 1.0000 Uani . . . . . . . C5 C 0.4544(4) 0.4602(2) 0.17297(19) 0.0252 1.0000 Uani . . . . . . . N6 N 0.2265(3) 0.5606(2) 0.15290(15) 0.0243 1.0000 Uani . . . . . . . N7 N 0.1614(3) 0.6317(2) 0.04622(15) 0.0282 1.0000 Uani . . . . . . . N8 N -0.0486(3) 0.7137(2) 0.05481(15) 0.0283 1.0000 Uani . . . . . . . C9 C -0.1165(4) 0.6945(2) 0.16770(17) 0.0225 1.0000 Uani . . . . . . . C10 C 0.0586(4) 0.5954(2) 0.23026(18) 0.0244 1.0000 Uani . . . . . . . C11 C -0.3421(4) 0.7733(2) 0.20521(17) 0.0222 1.0000 Uani . . . . . . . C12 C -0.3970(4) 0.7622(2) 0.32161(18) 0.0233 1.0000 Uani . . . . . . . C13 C -0.6178(4) 0.8305(2) 0.35701(17) 0.0223 1.0000 Uani . . . . . . . C14 C -0.7819(4) 0.9143(2) 0.27523(19) 0.0257 1.0000 Uani . . . . . . . C15 C -0.7255(4) 0.9288(2) 0.16000(18) 0.0254 1.0000 Uani . . . . . . . C16 C -0.5085(4) 0.8579(2) 0.12456(18) 0.0237 1.0000 Uani . . . . . . . C17 C -0.6813(4) 0.8147(2) 0.47931(18) 0.0237 1.0000 Uani . . . . . . . C18 C -0.5430(4) 0.8209(2) 0.56806(18) 0.0243 1.0000 Uani . . . . . . . N19 N -0.9094(3) 0.7930(2) 0.52140(16) 0.0314 1.0000 Uani . . . . . . . H32 H 0.7897 0.2245 0.1755 0.0266 1.0000 Uiso R . . . . . . H31 H 0.6297 0.0959 0.2192 0.0275 1.0000 Uiso R . . . . . . H41 H 0.2852 0.2732 0.2326 0.0287 1.0000 Uiso R . . . . . . H42 H 0.3824 0.2902 0.1018 0.0285 1.0000 Uiso R . . . . . . H52 H 0.5180 0.4692 0.2460 0.0290 1.0000 Uiso R . . . . . . H51 H 0.5694 0.4912 0.1088 0.0299 1.0000 Uiso R . . . . . . H101 H 0.0658 0.5588 0.3113 0.0297 1.0000 Uiso R . . . . . . H121 H -0.2828 0.7068 0.3790 0.0262 1.0000 Uiso R . . . . . . H141 H -0.9334 0.9607 0.2975 0.0292 1.0000 Uiso R . . . . . . H151 H -0.8395 0.9888 0.1049 0.0304 1.0000 Uiso R . . . . . . H161 H -0.4749 0.8638 0.0458 0.0270 1.0000 Uiso R . . . . . . H181 H -0.3791 0.8352 0.5678 0.0279 1.0000 Uiso 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 N1 0.0224(9) 0.0419(12) 0.0260(10) -0.0099(8) 0.0015(7) -0.0057(8) N2 0.0193(9) 0.0248(9) 0.0240(9) -0.0048(7) -0.0005(7) -0.0007(7) C3 0.0259(11) 0.0258(11) 0.0221(11) -0.0062(9) 0.0003(8) 0.0001(9) C4 0.0236(11) 0.0287(12) 0.0215(11) -0.0077(9) 0.0001(8) -0.0024(9) C5 0.0204(11) 0.0267(12) 0.0280(12) -0.0074(9) 0.0005(8) -0.0005(9) N6 0.0236(9) 0.0243(10) 0.0238(10) -0.0051(7) 0.0000(7) -0.0003(7) N7 0.0286(10) 0.0334(11) 0.0211(10) -0.0071(8) -0.0004(7) 0.0017(8) N8 0.0290(10) 0.0329(11) 0.0221(10) -0.0081(8) 0.0003(7) 0.0013(8) C9 0.0235(11) 0.0241(11) 0.0200(11) -0.0057(8) -0.0001(8) -0.0033(8) C10 0.0257(11) 0.0257(11) 0.0208(11) -0.0058(8) 0.0023(8) -0.0006(9) C11 0.0240(11) 0.0192(11) 0.0237(11) -0.0051(8) -0.0015(8) -0.0037(8) C12 0.0226(11) 0.0244(11) 0.0227(11) -0.0058(8) -0.0029(8) -0.0011(9) C13 0.0216(10) 0.0237(11) 0.0223(11) -0.0066(8) -0.0015(8) -0.0027(8) C14 0.0231(11) 0.0241(11) 0.0302(12) -0.0088(9) -0.0017(9) 0.0004(9) C15 0.0265(11) 0.0238(11) 0.0240(11) -0.0026(9) -0.0067(9) 0.0003(9) C16 0.0284(11) 0.0221(11) 0.0201(10) -0.0043(8) 0.0000(8) -0.0037(9) C17 0.0186(10) 0.0250(12) 0.0272(11) -0.0074(9) 0.0002(8) -0.0006(8) C18 0.0201(11) 0.0288(12) 0.0234(11) -0.0058(9) 0.0027(8) -0.0031(9) N19 0.0240(10) 0.0459(12) 0.0255(10) -0.0108(9) 0.0015(8) -0.0053(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.661(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . N19 2_566 1.318(3) yes N1 . N2 . 1.343(2) yes N2 . C18 2_566 1.348(3) yes N2 . C3 . 1.468(3) yes C3 . C4 . 1.521(3) yes C3 . H32 . 0.970 no C3 . H31 . 0.970 no C4 . C5 . 1.522(3) yes C4 . H41 . 0.987 no C4 . H42 . 0.989 no C5 . N6 . 1.465(3) yes C5 . H52 . 0.996 no C5 . H51 . 0.989 no N6 . N7 . 1.344(3) yes N6 . C10 . 1.344(3) yes N7 . N8 . 1.319(3) yes N8 . C9 . 1.367(3) yes C9 . C10 . 1.371(3) yes C9 . C11 . 1.469(3) yes C10 . H101 . 0.956 no C11 . C12 . 1.401(3) yes C11 . C16 . 1.401(3) yes C12 . C13 . 1.396(3) yes C12 . H121 . 0.969 no C13 . C14 . 1.399(3) yes C13 . C17 . 1.473(3) yes C14 . C15 . 1.384(3) yes C14 . H141 . 0.948 no C15 . C16 . 1.390(3) yes C15 . H151 . 0.965 no C16 . H161 . 0.946 no C17 . C18 . 1.373(3) yes C17 . N19 . 1.362(3) yes C18 . H181 . 0.940 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N19 2_566 N1 . N2 . 107.67(16) yes C18 2_566 N2 . N1 . 110.46(17) yes C18 2_566 N2 . C3 . 129.20(18) yes N1 . N2 . C3 . 120.32(17) yes N2 . C3 . C4 . 111.11(17) yes N2 . C3 . H32 . 106.9 no C4 . C3 . H32 . 111.5 no N2 . C3 . H31 . 108.0 no C4 . C3 . H31 . 110.9 no H32 . C3 . H31 . 108.3 no C3 . C4 . C5 . 110.78(17) yes C3 . C4 . H41 . 107.5 no C5 . C4 . H41 . 109.1 no C3 . C4 . H42 . 109.4 no C5 . C4 . H42 . 110.4 no H41 . C4 . H42 . 109.5 no C4 . C5 . N6 . 112.26(17) yes C4 . C5 . H52 . 111.0 no N6 . C5 . H52 . 107.0 no C4 . C5 . H51 . 107.6 no N6 . C5 . H51 . 108.4 no H52 . C5 . H51 . 110.5 no C5 . N6 . N7 . 120.72(17) yes C5 . N6 . C10 . 128.27(18) yes N7 . N6 . C10 . 111.01(17) yes N6 . N7 . N8 . 107.11(16) yes N7 . N8 . C9 . 108.82(17) yes N8 . C9 . C10 . 107.94(18) yes N8 . C9 . C11 . 121.80(18) yes C10 . C9 . C11 . 130.25(18) yes C9 . C10 . N6 . 105.11(18) yes C9 . C10 . H101 . 128.8 no N6 . C10 . H101 . 126.0 no C9 . C11 . C12 . 120.74(18) yes C9 . C11 . C16 . 120.15(18) yes C12 . C11 . C16 . 119.09(19) yes C11 . C12 . C13 . 120.48(19) yes C11 . C12 . H121 . 120.7 no C13 . C12 . H121 . 118.8 no C12 . C13 . C14 . 119.58(19) yes C12 . C13 . C17 . 120.90(18) yes C14 . C13 . C17 . 119.52(19) yes C13 . C14 . C15 . 120.1(2) yes C13 . C14 . H141 . 120.9 no C15 . C14 . H141 . 119.0 no C14 . C15 . C16 . 120.42(19) yes C14 . C15 . H151 . 118.9 no C16 . C15 . H151 . 120.7 no C11 . C16 . C15 . 120.26(19) yes C11 . C16 . H161 . 119.6 no C15 . C16 . H161 . 120.1 no C13 . C17 . C18 . 130.34(19) yes C13 . C17 . N19 . 121.52(18) yes C18 . C17 . N19 . 108.13(18) yes C17 . C18 . N2 2_566 105.12(18) yes C17 . C18 . H181 . 129.6 no N2 2_566 C18 . H181 . 125.3 no C17 . N19 . N1 2_566 108.62(17) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . N1 1_455 176 0.99 2.58 3.567(3) yes data_2MeOHH2O _database_code_depnum_ccdc_archive 'CCDC 881648' #TrackingRef 'Combined.cif' #============================================================================== _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 16.4629(10) _cell_length_b 10.8655(8) _cell_length_c 15.7413(11) _cell_angle_alpha 90 _cell_angle_beta 107.516(4) _cell_angle_gamma 90 _cell_volume 2685.2(3) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z x,-y,z+1/2 -x,y,-z+1/2 x+1/2,-y+1/2,z+1/2 -x+1/2,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C26 N12 O3 # Dc = 1.31 Fooo = 1176.00 Mu = 0.94 M = 264.18 # Found Formula = C26 H30 N12 O3 # Dc = 1.38 FOOO = 1176.00 Mu = 0.97 M = 279.30 _chemical_formula_sum 'C26 H30 N12 O3' _chemical_formula_moiety 'C26 H24 N12, 3(H2 O)' _chemical_compound_source synthesized _chemical_formula_weight 558.60 _cell_measurement_reflns_used 2788 _cell_measurement_theta_min 5 _cell_measurement_theta_max 26 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_max 0.080 _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.097 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.931 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 15939 _reflns_number_total 2774 _diffrn_reflns_av_R_equivalents 0.047 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2736 # Theoretical number of reflections is about 3899 _diffrn_reflns_theta_min 5.195 _diffrn_reflns_theta_max 26.439 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.910 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -20 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 2.43 _oxford_diffrn_Wilson_scale 58.64 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.45 _refine_diff_density_max 0.46 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 1919 _refine_ls_number_restraints 0 _refine_ls_number_parameters 186 _oxford_refine_ls_R_factor_ref 0.1124 _refine_ls_wR_factor_ref 0.1504 _refine_ls_goodness_of_fit_ref 0.9950 _refine_ls_shift/su_max 0.0002529 _refine_ls_shift/su_mean 0.0000222 # The values computed from all data _oxford_reflns_number_all 1919 _refine_ls_R_factor_all 0.1124 _refine_ls_wR_factor_all 0.1504 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1234 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_gt 0.1206 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 25.8 40.1 20.3 5.22 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.4617(2) 0.6066(3) 0.3855(2) 0.0710 1.0000 Uani . . . . . . . O2 O 1.0000 0.7456(4) 0.7500 0.0622 1.0000 Uani S T . . . . . N3 N 1.15026(19) 0.5931(3) 0.8121(2) 0.0427 1.0000 Uani . . . . . . . N4 N 1.2059(2) 0.6470(3) 0.8807(2) 0.0445 1.0000 Uani . . . . . . . N5 N 1.26530(19) 0.5610(3) 0.91840(19) 0.0395 1.0000 Uani . . . . . . . C6 C 0.6654(2) 0.5912(4) 0.5007(2) 0.0462 1.0000 Uani . . . . . . . C7 C 0.6721(2) 0.5247(4) 0.4188(2) 0.0434 1.0000 Uani . . . . . . . C8 C 0.7550(2) 0.5436(4) 0.3963(2) 0.0425 1.0000 Uani . . . . . . . N9 N 0.82300(18) 0.4613(3) 0.44645(18) 0.0405 1.0000 Uani . . . . . . . N10 N 0.8169(2) 0.3414(3) 0.4255(2) 0.0560 1.0000 Uani . . . . . . . N11 N 0.8830(2) 0.2856(3) 0.4820(2) 0.0540 1.0000 Uani . . . . . . . H11 H 0.4423 0.6598 0.4133 0.1053 1.0000 Uiso . . . . . . . C12 C 0.9305(2) 0.3709(4) 0.5383(2) 0.0393 1.0000 Uani . . . . . . . H12 H 0.4675 0.6525 0.3441 0.1052 1.0000 Uiso . . . . . . . C13 C 0.8929(2) 0.4837(4) 0.5150(2) 0.0396 1.0000 Uani . . . . . . . C14 C 1.0067(2) 0.3341(3) 0.6114(2) 0.0371 1.0000 Uani . . . . . . . C15 C 1.0548(2) 0.4213(4) 0.6710(2) 0.0377 1.0000 Uani . . . . . . . C16 C 1.1246(2) 0.3845(3) 0.7413(2) 0.0375 1.0000 Uani . . . . . . . C17 C 1.1743(2) 0.4728(3) 0.8069(2) 0.0366 1.0000 Uani . . . . . . . C18 C 1.2480(2) 0.4541(4) 0.8750(2) 0.0426 1.0000 Uani . . . . . . . C19 C 1.1464(2) 0.2599(4) 0.7513(2) 0.0433 1.0000 Uani . . . . . . . C20 C 1.0989(2) 0.1743(4) 0.6924(2) 0.0441 1.0000 Uani . . . . . . . C21 C 1.0292(2) 0.2104(4) 0.6234(2) 0.0422 1.0000 Uani . . . . . . . H24 H 1.0433 0.6997 0.7690 0.0911 1.0000 Uiso . . . . . . . H61 H 0.6654 0.6795 0.4914 0.0542 1.0000 Uiso R . . . . . . H62 H 0.6123 0.5673 0.5104 0.0541 1.0000 Uiso R . . . . . . H71 H 0.6645 0.4372 0.4263 0.0514 1.0000 Uiso R . . . . . . H72 H 0.6261 0.5549 0.3690 0.0507 1.0000 Uiso R . . . . . . H81 H 0.7733 0.6290 0.4076 0.0501 1.0000 Uiso R . . . . . . H82 H 0.7451 0.5240 0.3328 0.0500 1.0000 Uiso R . . . . . . H131 H 0.9115 0.5586 0.5404 0.0470 1.0000 Uiso R . . . . . . H151 H 1.0395 0.5045 0.6622 0.0440 1.0000 Uiso R . . . . . . H181 H 1.2803 0.3833 0.8894 0.0508 1.0000 Uiso R . . . . . . H191 H 1.1938 0.2352 0.7978 0.0507 1.0000 Uiso R . . . . . . H201 H 1.1129 0.0907 0.6995 0.0531 1.0000 Uiso R . . . . . . H211 H 0.9977 0.1512 0.5845 0.0492 1.0000 Uiso 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 O1 0.078(2) 0.058(2) 0.078(2) -0.0022(17) 0.0250(18) 0.0119(17) O2 0.050(2) 0.050(3) 0.082(3) 0.0000 0.013(2) 0.0000 N3 0.0379(18) 0.0433(19) 0.0412(19) -0.0003(15) 0.0036(15) -0.0001(16) N4 0.0451(19) 0.0420(19) 0.0439(19) -0.0016(16) 0.0094(16) -0.0008(17) N5 0.0352(18) 0.0392(19) 0.0399(17) -0.0027(15) 0.0050(14) -0.0068(15) C6 0.039(2) 0.052(2) 0.044(2) 0.004(2) 0.0062(18) 0.006(2) C7 0.0330(19) 0.051(2) 0.041(2) -0.0013(19) 0.0029(16) 0.005(2) C8 0.036(2) 0.049(2) 0.0388(19) 0.0059(19) 0.0045(17) 0.0066(19) N9 0.0330(18) 0.043(2) 0.0413(17) -0.0017(16) 0.0055(15) 0.0010(16) N10 0.048(2) 0.044(2) 0.062(2) -0.0091(18) -0.0058(18) 0.0046(18) N11 0.044(2) 0.046(2) 0.057(2) -0.0092(18) -0.0074(17) 0.0055(18) C12 0.034(2) 0.046(3) 0.038(2) -0.0038(19) 0.0104(17) 0.0026(18) C13 0.035(2) 0.043(2) 0.038(2) -0.0003(18) 0.0067(17) -0.0019(18) C14 0.036(2) 0.041(2) 0.035(2) 0.0005(18) 0.0109(17) 0.0023(18) C15 0.035(2) 0.041(2) 0.0367(19) -0.0001(17) 0.0104(17) 0.0038(17) C16 0.038(2) 0.043(2) 0.0314(19) -0.0020(17) 0.0104(18) -0.0044(18) C17 0.030(2) 0.041(2) 0.039(2) 0.0054(18) 0.0097(17) 0.0024(18) C18 0.038(2) 0.043(2) 0.043(2) -0.002(2) 0.0065(18) 0.0015(19) C19 0.043(2) 0.046(2) 0.037(2) 0.0013(19) 0.0054(18) 0.006(2) C20 0.048(2) 0.038(2) 0.043(2) 0.000(2) 0.010(2) 0.0042(19) C21 0.038(2) 0.044(2) 0.042(2) -0.0088(19) 0.0083(19) -0.0022(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.15241(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . H11 . 0.844 no O1 . H12 . 0.849 no O2 . H24 6_756 0.848 no O2 . H24 . 0.848 no N3 . N4 . 1.324(4) yes N3 . C17 . 1.375(5) yes N4 . N5 . 1.354(4) yes N5 . C6 6_756 1.469(5) yes N5 . C18 . 1.334(5) yes C6 . C7 . 1.510(5) yes C6 . H61 . 0.970 no C6 . H62 . 0.967 no C7 . C8 . 1.522(5) yes C7 . H71 . 0.972 no C7 . H72 . 0.969 no C8 . N9 . 1.464(5) yes C8 . H81 . 0.975 no C8 . H82 . 0.988 no N9 . N10 . 1.340(4) yes N9 . C13 . 1.342(4) yes N10 . N11 . 1.327(4) yes N11 . C12 . 1.355(5) yes C12 . C13 . 1.372(5) yes C12 . C14 . 1.480(5) yes C13 . H131 . 0.917 no C14 . C15 . 1.399(5) yes C14 . C21 . 1.392(5) yes C15 . C16 . 1.393(5) yes C15 . H151 . 0.938 no C16 . C17 . 1.465(5) yes C16 . C19 . 1.398(5) yes C17 . C18 . 1.370(5) yes C18 . H181 . 0.925 no C19 . C20 . 1.378(5) yes C19 . H191 . 0.934 no C20 . C21 . 1.379(5) yes C20 . H201 . 0.936 no C21 . H211 . 0.931 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H11 . O1 . H12 . 98.2 no H24 6_756 O2 . H24 . 107.9 no N4 . N3 . C17 . 109.2(3) yes N3 . N4 . N5 . 106.4(3) yes C6 6_756 N5 . N4 . 119.7(3) yes C6 6_756 N5 . C18 . 129.0(3) yes N4 . N5 . C18 . 111.2(3) yes N5 6_756 C6 . C7 . 113.3(3) yes N5 6_756 C6 . H61 . 108.5 no C7 . C6 . H61 . 110.0 no N5 6_756 C6 . H62 . 107.7 no C7 . C6 . H62 . 108.0 no H61 . C6 . H62 . 109.3 no C6 . C7 . C8 . 115.7(3) yes C6 . C7 . H71 . 108.6 no C8 . C7 . H71 . 108.6 no C6 . C7 . H72 . 106.8 no C8 . C7 . H72 . 107.7 no H71 . C7 . H72 . 109.4 no C7 . C8 . N9 . 112.7(3) yes C7 . C8 . H81 . 109.6 no N9 . C8 . H81 . 109.8 no C7 . C8 . H82 . 108.7 no N9 . C8 . H82 . 106.2 no H81 . C8 . H82 . 109.7 no C8 . N9 . N10 . 118.2(3) yes C8 . N9 . C13 . 130.9(3) yes N10 . N9 . C13 . 110.9(3) yes N9 . N10 . N11 . 107.1(3) yes N10 . N11 . C12 . 108.7(3) yes N11 . C12 . C13 . 108.1(3) yes N11 . C12 . C14 . 120.7(3) yes C13 . C12 . C14 . 131.1(3) yes C12 . C13 . N9 . 105.2(3) yes C12 . C13 . H131 . 127.7 no N9 . C13 . H131 . 127.1 no C12 . C14 . C15 . 121.0(3) yes C12 . C14 . C21 . 119.7(3) yes C15 . C14 . C21 . 119.3(3) yes C14 . C15 . C16 . 120.3(4) yes C14 . C15 . H151 . 118.7 no C16 . C15 . H151 . 121.0 no C15 . C16 . C17 . 121.6(3) yes C15 . C16 . C19 . 119.3(3) yes C17 . C16 . C19 . 119.0(3) yes C16 . C17 . N3 . 123.7(3) yes C16 . C17 . C18 . 129.0(3) yes N3 . C17 . C18 . 107.3(3) yes C17 . C18 . N5 . 105.9(3) yes C17 . C18 . H181 . 128.6 no N5 . C18 . H181 . 125.5 no C16 . C19 . C20 . 120.2(3) yes C16 . C19 . H191 . 119.5 no C20 . C19 . H191 . 120.3 no C19 . C20 . C21 . 120.5(4) yes C19 . C20 . H201 . 120.4 no C21 . C20 . H201 . 119.1 no C14 . C21 . C20 . 120.4(4) yes C14 . C21 . H211 . 120.4 no C20 . C21 . H211 . 119.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O1 . H11 . N11 3_455 175 0.84 2.15 2.993(5) yes O1 . H12 . O2 4_666 171 0.85 2.04 2.887(5) yes O2 . H24 . N3 . 178 0.85 2.05 2.893(5) yes C18 . H181 . N10 7_555 159 0.92 2.54 3.419(5) yes C19 . H191 . N10 7_555 177 0.93 2.53 3.461(5) yes data_7+BF4 _database_code_depnum_ccdc_archive 'CCDC 881649' #TrackingRef 'Combined.cif' #============================================================================== _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 7.67099(16) _cell_length_b 18.1327(5) _cell_length_c 14.7503(3) _cell_angle_alpha 90 _cell_angle_beta 90.726(2) _cell_angle_gamma 90 _cell_volume 2051.55(8) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C10 H10 B0.50 F2 N3 # Dc = 1.40 Fooo = 952.00 Mu = 9.52 M = 431.22 # Found Formula = C7 H11.50 B1 F4 N3.50 # Dc = 1.50 FOOO = 952.00 Mu = 12.77 M = 462.99 _chemical_formula_sum 'C28 H46 B4 F16 N14' _chemical_formula_moiety 'C24 H40 N12, 4(B F4), 2(C2 H3 N)' _chemical_compound_source synthesized _chemical_formula_weight 926.03 _cell_measurement_reflns_used 6288 _cell_measurement_theta_min 3.8601 _cell_measurement_theta_max 76.4459 _cell_measurement_temperature 150 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.277 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_T_min 0.55813 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_measurement_device 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrysAlis Pro, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis Pro, (Oxford Diffraction, 2010)' _computing_data_reduction 'CrysAlis Pro, (Oxford Diffraction, 2010)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 150 _diffrn_reflns_number 19667 _reflns_number_total 4292 _diffrn_reflns_av_R_equivalents 0.0555 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 4292 # Theoretical number of reflections is about 8638 _diffrn_reflns_theta_min 3.863 _diffrn_reflns_theta_max 76.638 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 75.106 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 3.05 _oxford_diffrn_Wilson_scale 0.02 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.53 _refine_diff_density_max 0.66 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 3845 _refine_ls_number_restraints 0 _refine_ls_number_parameters 280 _oxford_refine_ls_R_factor_ref 0.0608 _refine_ls_wR_factor_ref 0.0826 _refine_ls_goodness_of_fit_ref 0.9762 _refine_ls_shift/su_max 0.0006157 _refine_ls_shift/su_mean 0.0001051 # The values computed from all data _oxford_reflns_number_all 3845 _refine_ls_R_factor_all 0.0608 _refine_ls_wR_factor_all 0.0826 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3009 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_gt 0.0737 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.133E+04 0.196E+04 0.106E+04 329. ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.68646(18) 0.55193(8) -0.03610(9) 0.0363 1.0000 Uani . . . . . . B2 B 0.7923(3) 0.52645(15) -0.10628(18) 0.0262 1.0000 Uani . . . . . . F3 F 0.70467(18) 0.53454(9) -0.18871(9) 0.0382 1.0000 Uani . . . . . . F4 F 0.94336(19) 0.56799(9) -0.10735(11) 0.0470 1.0000 Uani . . . . . . F5 F 0.8301(2) 0.45293(8) -0.09099(11) 0.0512 1.0000 Uani . . . . . . F6 F 0.3450(2) 0.32755(11) 0.44871(12) 0.0644 1.0000 Uani . . . . . . B7 B 0.2876(4) 0.36055(16) 0.52645(19) 0.0313 1.0000 Uani . . . . . . F8 F 0.1880(2) 0.30977(10) 0.57317(11) 0.0570 1.0000 Uani . . . . . . F9 F 0.4308(2) 0.38028(11) 0.57894(12) 0.0626 1.0000 Uani . . . . . . F10 F 0.1924(3) 0.42080(12) 0.50730(19) 0.0975 1.0000 Uani . . . . . . N11 N 0.6089(2) 0.36513(10) 0.14582(13) 0.0267 1.0000 Uani . . . . . . N12 N 0.5934(3) 0.35605(11) 0.23458(14) 0.0312 1.0000 Uani . . . . . . N13 N 0.6473(3) 0.41992(10) 0.26849(13) 0.0294 1.0000 Uani . . . . . . C14 C 0.6978(3) 0.46843(12) 0.20433(15) 0.0251 1.0000 Uani . . . . . . C15 C 0.6707(3) 0.43228(12) 0.12427(16) 0.0271 1.0000 Uani . . . . . . C16 C 0.7593(3) 0.54518(12) 0.22229(16) 0.0278 1.0000 Uani . . . . . . C17 C 0.6245(3) 0.60180(12) 0.18951(16) 0.0266 1.0000 Uani . . . . . . C18 C 0.6827(3) 0.68133(12) 0.20795(16) 0.0269 1.0000 Uani . . . . . . C19 C 0.8331(3) 0.70427(12) 0.15221(15) 0.0232 1.0000 Uani . . . . . . N20 N 0.9261(2) 0.76690(10) 0.16820(13) 0.0270 1.0000 Uani . . . . . . N21 N 1.0498(3) 0.77871(11) 0.10853(13) 0.0298 1.0000 Uani . . . . . . N22 N 1.0367(2) 0.72159(10) 0.05322(12) 0.0254 1.0000 Uani . . . . . . C23 C 0.9077(3) 0.67499(12) 0.07643(15) 0.0239 1.0000 Uani . . . . . . C24 C 1.1483(3) 0.71726(14) -0.02642(16) 0.0298 1.0000 Uani . . . . . . C25 C 1.3366(3) 0.70034(13) -0.00088(16) 0.0298 1.0000 Uani . . . . . . C26 C 1.4492(3) 0.69530(13) -0.08516(17) 0.0327 1.0000 Uani . . . . . . C27 C 0.8985(4) 0.82012(15) 0.24038(18) 0.0416 1.0000 Uani . . . . . . C28 C 0.6508(4) 0.42941(16) 0.36767(17) 0.0475 1.0000 Uani . . . . . . N29 N 0.8072(4) 0.32512(16) -0.27536(19) 0.0570 1.0000 Uani . . . . . . C30 C 0.8123(3) 0.37814(18) -0.31685(19) 0.0417 1.0000 Uani . . . . . . C31 C 0.8186(4) 0.44507(18) -0.3708(2) 0.0524 1.0000 Uani . . . . . . H151 H 0.6891 0.4492 0.0648 0.0331 1.0000 Uiso R . . . . . H161 H 0.7750 0.5513 0.2869 0.0343 1.0000 Uiso R . . . . . H162 H 0.8707 0.5534 0.1922 0.0334 1.0000 Uiso R . . . . . H171 H 0.6064 0.5957 0.1242 0.0322 1.0000 Uiso R . . . . . H172 H 0.5156 0.5929 0.2218 0.0322 1.0000 Uiso R . . . . . H181 H 0.7129 0.6843 0.2726 0.0331 1.0000 Uiso R . . . . . H182 H 0.5856 0.7137 0.1960 0.0334 1.0000 Uiso R . . . . . H231 H 0.8806 0.6317 0.0458 0.0286 1.0000 Uiso R . . . . . H241 H 1.1429 0.7645 -0.0566 0.0365 1.0000 Uiso R . . . . . H242 H 1.1013 0.6782 -0.0660 0.0369 1.0000 Uiso R . . . . . H251 H 1.3817 0.7398 0.0380 0.0368 1.0000 Uiso R . . . . . H252 H 1.3420 0.6544 0.0316 0.0363 1.0000 Uiso R . . . . . H261 H 1.4421 0.7413 -0.1192 0.0385 1.0000 Uiso R . . . . . H262 H 1.5668 0.6858 -0.0680 0.0389 1.0000 Uiso R . . . . . H273 H 0.9918 0.8548 0.2386 0.0642 1.0000 Uiso R . . . . . H272 H 0.7884 0.8454 0.2325 0.0643 1.0000 Uiso R . . . . . H271 H 0.8985 0.7952 0.2971 0.0643 1.0000 Uiso R . . . . . H283 H 0.5957 0.4744 0.3834 0.0705 1.0000 Uiso R . . . . . H282 H 0.7690 0.4307 0.3900 0.0705 1.0000 Uiso R . . . . . H281 H 0.5902 0.3902 0.3965 0.0702 1.0000 Uiso R . . . . . H311 H 0.8275 0.4880 -0.3317 0.0802 1.0000 Uiso R . . . . . H312 H 0.9169 0.4437 -0.4094 0.0802 1.0000 Uiso R . . . . . H313 H 0.7149 0.4483 -0.4084 0.0799 1.0000 Uiso 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 F1 0.0336(8) 0.0451(9) 0.0304(7) -0.0048(6) 0.0051(6) 0.0027(7) B2 0.0221(13) 0.0287(14) 0.0278(13) 0.0000(11) 0.0019(10) -0.0007(10) F3 0.0337(8) 0.0533(9) 0.0275(7) 0.0024(7) -0.0018(6) -0.0010(7) F4 0.0303(8) 0.0601(10) 0.0504(9) 0.0033(8) -0.0001(7) -0.0159(7) F5 0.0693(11) 0.0307(8) 0.0536(10) 0.0057(7) 0.0052(8) 0.0135(8) F6 0.0575(11) 0.0858(14) 0.0503(10) -0.0337(10) 0.0164(8) -0.0230(10) B7 0.0333(15) 0.0305(15) 0.0300(14) -0.0019(11) 0.0022(12) -0.0013(12) F8 0.0566(10) 0.0737(12) 0.0406(9) 0.0128(9) -0.0056(8) -0.0324(9) F9 0.0569(11) 0.0791(13) 0.0517(10) -0.0083(9) -0.0070(8) -0.0327(10) F10 0.0862(16) 0.0531(13) 0.153(2) 0.0214(14) 0.0023(15) 0.0303(12) N11 0.0236(9) 0.0238(10) 0.0328(11) 0.0016(8) 0.0055(8) -0.0005(8) N12 0.0338(11) 0.0247(10) 0.0353(11) 0.0031(8) 0.0102(9) 0.0006(8) N13 0.0316(11) 0.0244(10) 0.0323(11) 0.0027(8) 0.0106(8) 0.0017(8) C14 0.0199(11) 0.0245(11) 0.0309(12) 0.0043(9) 0.0039(9) 0.0008(9) C15 0.0228(11) 0.0260(12) 0.0325(12) 0.0044(10) 0.0037(9) -0.0031(9) C16 0.0278(12) 0.0253(12) 0.0304(12) 0.0025(10) 0.0009(10) -0.0024(10) C17 0.0245(11) 0.0266(12) 0.0289(12) -0.0013(10) 0.0039(9) 0.0009(9) C18 0.0271(12) 0.0255(12) 0.0284(12) -0.0022(9) 0.0038(9) 0.0026(9) C19 0.0261(11) 0.0196(11) 0.0239(11) -0.0001(9) -0.0018(9) 0.0009(9) N20 0.0286(10) 0.0243(10) 0.0281(10) -0.0028(8) 0.0003(8) -0.0011(8) N21 0.0290(10) 0.0285(10) 0.0321(11) -0.0002(9) 0.0009(8) -0.0029(8) N22 0.0251(10) 0.0266(10) 0.0246(10) 0.0007(8) 0.0013(8) -0.0005(8) C23 0.0263(11) 0.0218(11) 0.0238(11) 0.0002(9) 0.0012(9) -0.0006(9) C24 0.0270(12) 0.0352(13) 0.0273(12) 0.0065(10) 0.0067(10) 0.0023(10) C25 0.0282(12) 0.0275(12) 0.0337(13) -0.0007(10) -0.0009(10) -0.0022(10) C26 0.0265(12) 0.0265(12) 0.0453(14) -0.0034(11) 0.0063(11) -0.0041(10) C27 0.0516(17) 0.0339(14) 0.0394(15) -0.0168(12) 0.0060(12) -0.0059(12) C28 0.072(2) 0.0382(15) 0.0331(14) 0.0033(12) 0.0169(14) -0.0026(14) N29 0.0575(17) 0.0556(17) 0.0577(17) -0.0065(14) -0.0068(13) 0.0122(14) C30 0.0321(14) 0.0524(18) 0.0406(15) -0.0175(14) -0.0011(12) 0.0062(13) C31 0.0494(18) 0.058(2) 0.0494(18) -0.0023(15) 0.0008(14) -0.0044(15) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.88(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . B2 . 1.402(3) yes B2 . F3 . 1.390(3) yes B2 . F4 . 1.383(3) yes B2 . F5 . 1.382(3) yes F6 . B7 . 1.371(3) yes B7 . F8 . 1.385(3) yes B7 . F9 . 1.384(3) yes B7 . F10 . 1.342(3) yes N11 . C26 2_765 1.480(3) yes N11 . N12 . 1.326(3) yes N11 . C15 . 1.346(3) yes N12 . N13 . 1.326(3) yes N13 . C14 . 1.352(3) yes N13 . C28 . 1.473(3) yes C14 . C15 . 1.364(3) yes C14 . C16 . 1.492(3) yes C15 . H151 . 0.942 no C16 . C17 . 1.531(3) yes C16 . H161 . 0.965 no C16 . H162 . 0.979 no C17 . C18 . 1.533(3) yes C17 . H171 . 0.978 no C17 . H172 . 0.980 no C18 . C19 . 1.484(3) yes C18 . H181 . 0.980 no C18 . H182 . 0.963 no C19 . N20 . 1.360(3) yes C19 . C23 . 1.369(3) yes N20 . N21 . 1.320(3) yes N20 . C27 . 1.454(3) yes N21 . N22 . 1.322(3) yes N22 . C23 . 1.349(3) yes N22 . C24 . 1.464(3) yes C23 . H231 . 0.928 no C24 . C25 . 1.520(3) yes C24 . H241 . 0.966 no C24 . H242 . 0.983 no C25 . C26 . 1.525(3) yes C25 . H251 . 0.978 no C25 . H252 . 0.961 no C26 . H261 . 0.974 no C26 . H262 . 0.950 no C27 . H273 . 0.953 no C27 . H272 . 0.967 no C27 . H271 . 0.951 no C28 . H283 . 0.949 no C28 . H282 . 0.961 no C28 . H281 . 0.953 no N29 . C30 . 1.141(4) yes C30 . C31 . 1.452(4) yes C31 . H311 . 0.971 no C31 . H312 . 0.952 no C31 . H313 . 0.965 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag F1 . B2 . F3 . 109.47(19) yes F1 . B2 . F4 . 108.8(2) yes F3 . B2 . F4 . 109.2(2) yes F1 . B2 . F5 . 108.6(2) yes F3 . B2 . F5 . 110.0(2) yes F4 . B2 . F5 . 110.7(2) yes F6 . B7 . F8 . 108.1(2) yes F6 . B7 . F9 . 108.6(2) yes F8 . B7 . F9 . 109.4(2) yes F6 . B7 . F10 . 111.0(3) yes F8 . B7 . F10 . 110.1(2) yes F9 . B7 . F10 . 109.5(2) yes C26 2_765 N11 . N12 . 118.36(19) yes C26 2_765 N11 . C15 . 129.1(2) yes N12 . N11 . C15 . 112.43(19) yes N11 . N12 . N13 . 103.45(18) yes N12 . N13 . C14 . 113.27(19) yes N12 . N13 . C28 . 118.58(19) yes C14 . N13 . C28 . 128.1(2) yes N13 . C14 . C15 . 104.6(2) yes N13 . C14 . C16 . 125.1(2) yes C15 . C14 . C16 . 130.2(2) yes C14 . C15 . N11 . 106.3(2) yes C14 . C15 . H151 . 128.8 no N11 . C15 . H151 . 124.9 no C14 . C16 . C17 . 111.00(19) yes C14 . C16 . H161 . 108.6 no C17 . C16 . H161 . 108.0 no C14 . C16 . H162 . 109.7 no C17 . C16 . H162 . 110.2 no H161 . C16 . H162 . 109.3 no C16 . C17 . C18 . 112.37(19) yes C16 . C17 . H171 . 108.8 no C18 . C17 . H171 . 108.5 no C16 . C17 . H172 . 108.3 no C18 . C17 . H172 . 108.5 no H171 . C17 . H172 . 110.4 no C17 . C18 . C19 . 113.08(18) yes C17 . C18 . H181 . 106.8 no C19 . C18 . H181 . 110.4 no C17 . C18 . H182 . 108.5 no C19 . C18 . H182 . 109.4 no H181 . C18 . H182 . 108.5 no C18 . C19 . N20 . 123.19(19) yes C18 . C19 . C23 . 132.8(2) yes N20 . C19 . C23 . 103.98(19) yes C19 . N20 . N21 . 113.56(18) yes C19 . N20 . C27 . 126.9(2) yes N21 . N20 . C27 . 119.5(2) yes N20 . N21 . N22 . 103.59(17) yes N21 . N22 . C23 . 112.61(18) yes N21 . N22 . C24 . 119.77(19) yes C23 . N22 . C24 . 127.5(2) yes C19 . C23 . N22 . 106.25(19) yes C19 . C23 . H231 . 129.2 no N22 . C23 . H231 . 124.5 no N22 . C24 . C25 . 112.07(19) yes N22 . C24 . H241 . 107.4 no C25 . C24 . H241 . 109.2 no N22 . C24 . H242 . 107.5 no C25 . C24 . H242 . 110.0 no H241 . C24 . H242 . 110.6 no C24 . C25 . C26 . 110.9(2) yes C24 . C25 . H251 . 109.0 no C26 . C25 . H251 . 108.8 no C24 . C25 . H252 . 109.5 no C26 . C25 . H252 . 109.5 no H251 . C25 . H252 . 109.2 no C25 . C26 . N11 2_765 111.60(19) yes C25 . C26 . H261 . 109.9 no N11 2_765 C26 . H261 . 107.9 no C25 . C26 . H262 . 109.8 no N11 2_765 C26 . H262 . 107.7 no H261 . C26 . H262 . 109.8 no N20 . C27 . H273 . 107.6 no N20 . C27 . H272 . 111.1 no H273 . C27 . H272 . 109.9 no N20 . C27 . H271 . 109.3 no H273 . C27 . H271 . 110.3 no H272 . C27 . H271 . 108.8 no N13 . C28 . H283 . 109.9 no N13 . C28 . H282 . 110.4 no H283 . C28 . H282 . 108.5 no N13 . C28 . H281 . 110.7 no H283 . C28 . H281 . 108.2 no H282 . C28 . H281 . 109.2 no N29 . C30 . C31 . 179.2(3) yes C30 . C31 . H311 . 110.3 no C30 . C31 . H312 . 109.7 no H311 . C31 . H312 . 109.0 no C30 . C31 . H313 . 109.4 no H311 . C31 . H313 . 110.1 no H312 . C31 . H313 . 108.2 no