#------------------------------------------------------------------------------ #$Date: 2012-07-07 14:03:05 +0100 (Sat, 07 Jul 2012) $ #$Revision: 62325 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/78/1507837.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1507837 loop_ _publ_author_name 'Hutt, Johnathon T.' 'Jo, Junyong' 'Olasz, Andr\'as' 'Chen, Chun-Hsing' 'Lee, Dongwhan' 'Aron, Zachary D.' _publ_section_title ; Fluorescence Switching of Imidazo[1,5-a]pyridinium Ions: pH-Sensors with Dual Emission Pathways ; _journal_issue 12 _journal_name_full 'Organic Letters' _journal_page_first 3162 _journal_volume 14 _journal_year 2012 _chemical_formula_moiety 'C17 H20 F6 N3 P1' _chemical_formula_sum 'C17 H20 F6 N3 P' _chemical_formula_weight 411.33 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _audit_creation_date 12-02-28 _audit_creation_method CRYSTALS_ver_14.40 _cell_angle_alpha 90 _cell_angle_beta 99.3450(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 24.3719(19) _cell_length_b 10.2345(7) _cell_length_c 14.8466(11) _cell_measurement_reflns_used 7008 _cell_measurement_temperature 150 _cell_measurement_theta_max 30 _cell_measurement_theta_min 3 _cell_volume 3654.1(5) _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 20229 _diffrn_reflns_theta_full 30.028 _diffrn_reflns_theta_max 30.028 _diffrn_reflns_theta_min 2.163 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1696.000 _exptl_crystal_size_max 0.376 _exptl_crystal_size_mid 0.323 _exptl_crystal_size_min 0.174 _refine_diff_density_max 0.83 _refine_diff_density_min -0.83 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0111 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 296 _refine_ls_number_reflns 5255 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0877 _refine_ls_shift/su_max 0.0178595 _refine_ls_shift/su_mean 0.0018080 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.11P)^2^ + 9.60P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.2454 _refine_ls_wR_factor_gt 0.2263 _refine_ls_wR_factor_ref 0.2412 _reflns_limit_h_max 33 _reflns_limit_h_min -34 _reflns_limit_k_max 14 _reflns_limit_k_min 0 _reflns_limit_l_max 20 _reflns_limit_l_min 0 _reflns_number_gt 4627 _reflns_number_total 5333 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0960 _oxford_refine_ls_scale 0.07627(4) _oxford_reflns_number_all 5320 _oxford_reflns_threshold_expression_ref I>0.0\s(I) _oxford_structure_analysis_title 'mo_12023_0m in C2/c' _[local]_cod_data_source_file ol3012524_si_001.cif _[local]_cod_data_source_block 12023 _[local]_cod_cif_authors_sg_H-M 'C 1 2/c 1 ' _[local]_cod_chemical_formula_sum_orig 'C17 H20 F6 N3 P1' _cod_database_code 1507837 _iucr_refine_instruction_details_constraints ; BLOCK CONT SCALE CONT P ( 1 ,X'S,U'S) CONT F ( 1 ,X'S,U'S) UNTIL F ( 6 ) CONT F ( 11 ,X'S,U[ISO]) UNTIL F ( 61 ) CONT N ( 1 ,X'S,U'S) UNTIL N ( 31 ) CONT C ( 1 ,X'S,U'S) UNTIL C ( 13 ) CONT C ( 14 ,X'S,U'S) UNTIL C ( 17 ) CONT C ( 18 ,X'S,U[ISO]) UNTIL C ( 21 ) SUMFIX PART(1001,OCC) AND PART(1002,OCC) SUMFIX PART(1003,OCC) AND PART(1004,OCC) SUMFIX PART(2001,OCC) AND PART(2002,OCC) RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) H ( 153,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S) H ( 173,X'S) RIDE C ( 18,X'S) H ( 181,X'S) H ( 182,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) H ( 193,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S) H ( 213,X'S) END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) U(IJ)'S 0.0, 0.010000 = F(1) TO F(3) DISTANCE 1.540000 , 0.050000 = C(20) TO C(21) END ; 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_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 P1 P 0.58063(3) 0.16862(7) 0.65094(6) 0.0489 1.0000 Uani . . . . . F1 F 0.5511(3) 0.2961(4) 0.6804(4) 0.1179 0.665(4) Uani . U P 1 1 F2 F 0.5816(3) 0.2246(4) 0.5558(2) 0.1063 0.665(4) Uani . . P 1 1 F3 F 0.63814(19) 0.2293(4) 0.6828(3) 0.1001 0.665(4) Uani . U P 1 1 F4 F 0.60746(16) 0.0354(3) 0.6277(3) 0.0767 0.665(4) Uani . . P 1 1 F5 F 0.5762(2) 0.1149(3) 0.7522(2) 0.0902 0.665(4) Uani . . P 1 1 F6 F 0.52066(16) 0.0984(4) 0.6225(4) 0.1048 0.665(4) Uani . . P 1 1 F11 F 0.5333(3) 0.2513(7) 0.5926(5) 0.0665(17) 0.335(4) Uiso . . P 1 2 F21 F 0.6265(3) 0.2404(7) 0.5919(5) 0.0704(19) 0.335(4) Uiso . . P 1 2 F31 F 0.5941(3) 0.2886(7) 0.7153(5) 0.0643(17) 0.335(4) Uiso . . P 1 2 F41 F 0.6350(4) 0.0988(10) 0.7016(6) 0.098(3) 0.335(4) Uiso . . P 1 2 F51 F 0.5421(3) 0.0917(7) 0.6957(6) 0.0708(18) 0.335(4) Uiso . . P 1 2 F61 F 0.5719(4) 0.0624(11) 0.5664(7) 0.107(3) 0.335(4) Uiso . . P 1 2 N1 N 0.45637(9) 0.33731(18) 0.42617(14) 0.0347 1.0000 Uani . . . . . N2 N 0.52102(9) 0.2359(2) 0.37001(14) 0.0379 1.0000 Uani . . . . . N3 N 0.2662(2) 0.4462(6) 0.5814(4) 0.0556 0.777(10) Uani . . P 1 3 N31 N 0.2546(7) 0.3961(16) 0.5614(14) 0.0480 0.223(10) Uani . . P 1 4 C1 C 0.40756(10) 0.3611(2) 0.46601(17) 0.0372 1.0000 Uani . . . . . C2 C 0.39452(10) 0.2831(2) 0.53588(17) 0.0387 1.0000 Uani . . . . . C3 C 0.34703(11) 0.3064(3) 0.57260(17) 0.0436 1.0000 Uani . . . . . C4 C 0.31142(12) 0.4118(3) 0.5421(2) 0.0526 1.0000 Uani . . . . . C5 C 0.32715(13) 0.4926(3) 0.4733(2) 0.0540 1.0000 Uani . . . . . C6 C 0.37399(12) 0.4663(3) 0.43569(19) 0.0470 1.0000 Uani . . . . . C7 C 0.47536(11) 0.2193(2) 0.40826(17) 0.0383 1.0000 Uani . . . . . C8 C 0.53114(10) 0.3698(2) 0.36285(17) 0.0376 1.0000 Uani . . . . . C9 C 0.55450(13) 0.1420(3) 0.3378(2) 0.0468 1.0000 Uani . . . . . C10 C 0.59787(13) 0.1830(3) 0.3001(2) 0.0512 1.0000 Uani . . . . . C11 C 0.61033(12) 0.3186(3) 0.2929(2) 0.0515 1.0000 Uani . . . . . C12 C 0.57763(12) 0.4105(3) 0.3229(2) 0.0474 1.0000 Uani . . . . . C13 C 0.48996(11) 0.4320(2) 0.39813(17) 0.0388 1.0000 Uani . . . . . C14 C 0.23551(17) 0.5668(5) 0.5614(3) 0.0520 0.777(10) Uani . . P 1 3 C15 C 0.19318(17) 0.5599(5) 0.4738(3) 0.0590 0.777(10) Uani . . P 1 3 C16 C 0.24054(14) 0.3434(5) 0.6354(2) 0.0593 0.871(9) Uani . . P 2 2 C17 C 0.25534(19) 0.3799(6) 0.7351(3) 0.0764 0.871(9) Uani . . P 2 2 C18 C 0.2130(6) 0.4941(14) 0.5174(10) 0.049(4) 0.223(10) Uiso . . P 1 4 C19 C 0.2255(10) 0.630(3) 0.5483(17) 0.078(6) 0.223(10) Uiso . . P 1 4 C20 C 0.2690(10) 0.403(2) 0.6865(18) 0.052(7) 0.129(9) Uiso D . P 2 1 C21 C 0.2306(15) 0.286(4) 0.678(3) 0.082(11) 0.129(9) Uiso D . P 2 1 H21 H 0.4187 0.2136 0.5587 0.0471 1.0000 Uiso R . . . . H31 H 0.3381 0.2505 0.6192 0.0512 1.0000 Uiso R . . . . H51 H 0.3053 0.5675 0.4540 0.0592 1.0000 Uiso R . . . . H61 H 0.3832 0.5203 0.3883 0.0554 1.0000 Uiso R . . . . H71 H 0.4593 0.1378 0.4200 0.0452 1.0000 Uiso R . . . . H91 H 0.5465 0.0517 0.3424 0.0556 1.0000 Uiso R . . . . H101 H 0.6205 0.1204 0.2764 0.0608 1.0000 Uiso R . . . . H111 H 0.6422 0.3442 0.2681 0.0613 1.0000 Uiso R . . . . H121 H 0.5856 0.5007 0.3177 0.0560 1.0000 Uiso R . . . . H131 H 0.4855 0.5238 0.4026 0.0474 1.0000 Uiso R . . . . H141 H 0.2605 0.6365 0.5560 0.0561 0.777(10) Uiso R . P 1 3 H142 H 0.2153 0.5851 0.6096 0.0561 0.777(10) Uiso R . P 1 3 H151 H 0.1737 0.6403 0.4632 0.0641 0.777(10) Uiso R . P 1 3 H152 H 0.2127 0.5427 0.4247 0.0641 0.777(10) Uiso R . P 1 3 H153 H 0.1675 0.4913 0.4783 0.0641 0.777(10) Uiso R . P 1 3 H171 H 0.2398 0.3164 0.7702 0.0864 0.871(9) Uiso R . P 2 2 H172 H 0.2946 0.3817 0.7527 0.0864 0.871(9) Uiso R . P 2 2 H173 H 0.2404 0.4634 0.7451 0.0864 0.871(9) Uiso R . P 2 2 H181 H 0.1767 0.4736 0.5290 0.0788 0.223(10) Uiso R . P 1 4 H182 H 0.2132 0.4919 0.4535 0.0788 0.223(10) Uiso R . P 1 4 H191 H 0.2009 0.6958 0.5208 0.1007 0.223(10) Uiso R . P 1 4 H192 H 0.2256 0.6294 0.6123 0.1007 0.223(10) Uiso R . P 1 4 H193 H 0.2620 0.6476 0.5368 0.1007 0.223(10) Uiso R . P 1 4 H211 H 0.2346 0.2537 0.7386 0.0865 0.129(9) Uiso R . P 2 1 H212 H 0.1938 0.3172 0.6597 0.0865 0.129(9) Uiso R . P 2 1 H213 H 0.2380 0.2180 0.6381 0.0865 0.129(9) Uiso R . P 2 1 H201 H 0.2617 0.4709 0.7263 0.0646 0.129(9) Uiso R . P 2 1 H202 H 0.3059 0.3717 0.7047 0.0646 0.129(9) Uiso R . P 2 1 H161 H 0.2533 0.2560 0.6319 0.0652 0.871(9) Uiso R . P 2 2 H162 H 0.2011 0.3449 0.6229 0.0652 0.871(9) Uiso R . P 2 2 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 P1 0.0559(5) 0.0340(4) 0.0581(5) 0.0100(3) 0.0134(3) -0.0025(3) F1 0.170(5) 0.0415(17) 0.167(4) 0.021(2) 0.101(4) 0.028(2) F2 0.194(5) 0.077(3) 0.0440(16) 0.0256(16) 0.007(2) -0.020(3) F3 0.096(3) 0.081(3) 0.120(3) -0.007(2) 0.005(2) -0.042(2) F4 0.088(2) 0.0426(15) 0.117(3) -0.0036(16) 0.068(2) -0.0013(15) F5 0.168(4) 0.0505(17) 0.064(2) 0.0104(15) 0.055(2) -0.016(2) F6 0.060(2) 0.079(3) 0.169(5) 0.017(3) 0.001(2) -0.0207(19) N1 0.0415(10) 0.0253(9) 0.0379(9) -0.0004(7) 0.0085(8) -0.0037(7) N2 0.0446(11) 0.0287(9) 0.0401(10) -0.0052(7) 0.0059(8) -0.0027(8) N3 0.052(2) 0.064(3) 0.056(2) 0.019(2) 0.0247(19) 0.004(2) N31 0.039(7) 0.039(8) 0.070(10) 0.015(6) 0.020(6) 0.003(5) C1 0.0418(12) 0.0309(10) 0.0398(11) 0.0039(9) 0.0099(9) -0.0029(9) C2 0.0420(12) 0.0353(11) 0.0379(11) 0.0066(9) 0.0042(9) -0.0043(9) C3 0.0456(13) 0.0478(14) 0.0376(12) 0.0127(10) 0.0077(10) -0.0057(11) C4 0.0472(14) 0.0667(19) 0.0472(14) 0.0187(13) 0.0173(11) 0.0078(13) C5 0.0533(16) 0.0600(18) 0.0532(15) 0.0220(14) 0.0225(13) 0.0147(13) C6 0.0533(15) 0.0449(14) 0.0461(13) 0.0158(11) 0.0180(11) 0.0060(11) C7 0.0487(13) 0.0243(10) 0.0422(12) -0.0017(8) 0.0084(10) -0.0049(9) C8 0.0430(12) 0.0304(11) 0.0395(11) -0.0048(9) 0.0067(9) -0.0065(9) C9 0.0568(15) 0.0342(12) 0.0497(14) -0.0078(10) 0.0099(12) 0.0039(11) C10 0.0504(15) 0.0530(16) 0.0508(15) -0.0117(12) 0.0105(12) 0.0074(12) C11 0.0438(14) 0.0585(17) 0.0544(16) -0.0093(13) 0.0143(12) -0.0061(12) C12 0.0475(14) 0.0426(14) 0.0543(15) -0.0064(11) 0.0147(12) -0.0104(11) C13 0.0463(13) 0.0254(10) 0.0466(12) -0.0016(9) 0.0132(10) -0.0064(9) C14 0.0429(19) 0.070(3) 0.0451(19) 0.0044(18) 0.0126(14) 0.0041(18) C15 0.048(2) 0.076(3) 0.053(2) 0.004(2) 0.0073(16) -0.0038(19) C16 0.0390(16) 0.098(3) 0.0420(17) 0.0177(18) 0.0101(12) -0.0069(17) C17 0.065(2) 0.121(4) 0.045(2) 0.011(2) 0.0121(17) -0.002(3) 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' F 0.0171 0.0103 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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag F1 P1 F2 91.3(3) yes F1 P1 F3 90.8(3) yes F2 P1 F3 89.0(3) yes F1 P1 F4 175.12(19) yes F2 P1 F4 93.0(2) yes F3 P1 F4 91.5(2) yes F1 P1 F5 85.5(2) yes F2 P1 F5 176.4(3) yes F3 P1 F5 92.7(3) yes F4 P1 F5 90.1(2) yes F1 P1 F6 90.4(3) yes F2 P1 F6 94.3(3) yes F3 P1 F6 176.5(3) yes F4 P1 F6 87.0(2) yes F5 P1 F6 84.1(3) yes F11 P1 F21 88.2(4) yes F11 P1 F31 88.7(4) yes F21 P1 F31 83.4(4) yes F11 P1 F41 170.6(4) yes F21 P1 F41 82.5(4) yes F31 P1 F41 89.3(5) yes F11 P1 F51 94.1(4) yes F21 P1 F51 172.9(4) yes F31 P1 F51 103.4(4) yes F41 P1 F51 95.2(5) yes F11 P1 F61 86.7(5) yes F21 P1 F61 84.6(4) yes F31 P1 F61 167.3(4) yes F41 P1 F61 93.3(5) yes F51 P1 F61 88.8(5) yes C1 N1 C7 125.0(2) yes C1 N1 C13 125.4(2) yes C7 N1 C13 109.5(2) yes C7 N2 C8 109.0(2) yes C7 N2 C9 129.1(2) yes C8 N2 C9 121.9(2) yes C4 N3 C14 123.7(4) yes C4 N3 C20 115.5(10) yes C14 N3 C20 111.9(10) yes C4 N3 C14 123.7(4) yes C4 N3 C16 118.3(5) yes C14 N3 C16 117.1(4) yes C4 N31 C18 115.8(12) yes C4 N31 C20 99.3(13) yes C18 N31 C20 114.9(14) yes C4 N31 C16 126.1(13) yes C4 N31 C18 115.8(12) yes C16 N31 C18 112.8(13) yes N1 C1 C2 121.2(2) yes N1 C1 C6 119.0(2) yes C2 C1 C6 119.8(2) yes C1 C2 C3 120.4(2) yes C1 C2 H21 119.6 no C3 C2 H21 120.0 no C2 C3 C4 121.1(2) yes C2 C3 H31 119.3 no C4 C3 H31 119.5 no C3 C4 N3 123.5(3) yes C3 C4 C5 117.0(3) yes N3 C4 C5 119.2(3) yes N31 C4 C3 113.8(7) yes N31 C4 C5 125.5(7) yes C3 C4 C5 117.0(3) yes C4 C5 C6 121.2(3) yes C4 C5 H51 119.0 no C6 C5 H51 119.8 no C1 C6 C5 120.4(2) yes C1 C6 H61 119.7 no C5 C6 H61 119.9 no N2 C7 N1 108.0(2) yes N2 C7 H71 125.7 no N1 C7 H71 126.3 no N2 C8 C12 118.7(2) yes N2 C8 C13 106.1(2) yes C12 C8 C13 135.2(2) yes N2 C9 C10 118.2(3) yes N2 C9 H91 120.5 no C10 C9 H91 121.3 no C9 C10 C11 121.8(3) yes C9 C10 H101 119.2 no C11 C10 H101 119.0 no C10 C11 C12 120.4(3) yes C10 C11 H111 119.7 no C12 C11 H111 119.9 no C8 C12 C11 119.0(3) yes C8 C12 H121 120.4 no C11 C12 H121 120.6 no N1 C13 C8 107.4(2) yes N1 C13 H131 126.5 no C8 C13 H131 126.1 no N3 C14 C15 113.0(5) yes N3 C14 H141 109.8 no C15 C14 H141 108.5 no N3 C14 H142 109.1 no C15 C14 H142 106.8 no H141 C14 H142 109.5 no C14 C15 H151 110.7 no C14 C15 H152 108.0 no H151 C15 H152 109.5 no C14 C15 H153 109.7 no H151 C15 H153 109.5 no H152 C15 H153 109.5 no N3 C16 C17 107.0(4) yes N3 C16 H161 117.2 no C17 C16 H161 104.9 no N3 C16 H162 112.1 no C17 C16 H162 105.1 no H161 C16 H162 109.5 no N31 C16 C17 131.4(9) yes N31 C16 H161 102.1 no C17 C16 H161 104.9 no N31 C16 H162 102.8 no C17 C16 H162 105.1 no H161 C16 H162 109.5 no C16 C17 H171 108.4 no C16 C17 H172 110.1 no H171 C17 H172 109.5 no C16 C17 H173 109.8 no H171 C17 H173 109.5 no H172 C17 H173 109.5 no N31 C18 C19 113.7(17) yes N31 C18 H181 110.8 no C19 C18 H181 107.6 no N31 C18 H182 107.8 no C19 C18 H182 107.4 no H181 C18 H182 109.5 no C18 C19 H191 116.6 no C18 C19 H192 105.7 no H191 C19 H192 109.5 no C18 C19 H193 105.9 no H191 C19 H193 109.5 no H192 C19 H193 109.5 no N3 C20 C21 102(2) yes N3 C20 H201 114.6 no C21 C20 H201 117.3 no N3 C20 H202 104.8 no C21 C20 H202 107.7 no H201 C20 H202 109.5 no N31 C20 C21 83(2) yes N31 C20 H201 129.2 no C21 C20 H201 117.3 no N31 C20 H202 107.0 no C21 C20 H202 107.7 no H201 C20 H202 109.5 no C20 C21 H211 103.3 no C20 C21 H212 107.6 no H211 C21 H212 109.5 no C20 C21 H213 117.2 no H211 C21 H213 109.5 no H212 C21 H213 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag P1 F1 1.585(4) yes P1 F2 1.528(3) yes P1 F3 1.536(4) yes P1 F4 1.575(3) yes P1 F5 1.622(3) yes P1 F6 1.622(4) yes P1 F11 1.572(7) yes P1 F21 1.695(7) yes P1 F31 1.558(7) yes P1 F41 1.584(9) yes P1 F51 1.464(7) yes P1 F61 1.649(10) yes N1 C1 1.433(3) yes N1 C7 1.335(3) yes N1 C13 1.376(3) yes N2 C7 1.340(3) yes N2 C8 1.399(3) yes N2 C9 1.395(3) yes N3 C4 1.374(6) yes N3 C14 1.449(8) yes N3 C20 1.61(3) yes N3 C4 1.374(6) yes N3 C14 1.449(8) yes N3 C16 1.518(6) yes N31 C4 1.468(16) yes N31 C18 1.50(2) yes N31 C20 1.84(3) yes N31 C4 1.468(16) yes N31 C16 1.318(18) yes N31 C18 1.50(2) yes C1 C2 1.386(3) yes C1 C6 1.382(4) yes C2 C3 1.378(4) yes C2 H21 0.950 no C3 C4 1.412(4) yes C3 H31 0.950 no C4 C5 1.415(4) yes C4 C5 1.415(4) yes C5 C6 1.376(4) yes C5 H51 0.950 no C6 H61 0.950 no C7 H71 0.950 no C8 C12 1.423(4) yes C8 C13 1.363(4) yes C9 C10 1.341(4) yes C9 H91 0.950 no C10 C11 1.428(5) yes C10 H101 0.950 no C11 C12 1.354(4) yes C11 H111 0.950 no C12 H121 0.950 no C13 H131 0.950 no C14 C15 1.525(6) yes C14 H141 0.950 no C14 H142 0.950 no C15 H151 0.950 no C15 H152 0.950 no C15 H153 0.950 no C16 C17 1.512(6) yes C16 H161 0.950 no C16 H162 0.950 no C16 C17 1.512(6) yes C16 H161 0.950 no C16 H162 0.950 no C17 H171 0.950 no C17 H172 0.950 no C17 H173 0.950 no C18 C19 1.48(3) yes C18 H181 0.950 no C18 H182 0.950 no C19 H191 0.950 no C19 H192 0.950 no C19 H193 0.950 no C20 C21 1.51(3) yes C20 H201 0.950 no C20 H202 0.950 no C20 C21 1.51(3) yes C20 H201 0.950 no C20 H202 0.950 no C21 H211 0.950 no C21 H212 0.950 no C21 H213 0.950 no 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_publ_flag C7 N1 C1 C2 39.6(4) no C7 N1 C1 C6 -142.3(3) no C13 N1 C1 C2 -142.3(2) no C13 N1 C1 C6 35.7(4) no C1 N1 C7 N2 179.0(2) no C13 N1 C7 N2 0.7(3) no C1 N1 C13 C8 -179.0(2) no C7 N1 C13 C8 -0.7(3) no C8 N2 C7 N1 -0.4(3) no C9 N2 C7 N1 -178.4(2) no C7 N2 C8 C12 -179.3(2) no C7 N2 C8 C13 0.0(3) no C9 N2 C8 C12 -1.1(4) no C9 N2 C8 C13 178.2(2) no C7 N2 C9 C10 178.6(3) no C8 N2 C9 C10 0.8(4) no C14 N3 C4 C3 168.7(4) no C14 N3 C4 C5 -4.8(7) no C4 N3 C14 C15 81.6(6) no N1 C1 C2 C3 -179.2(2) no C6 C1 C2 C3 2.8(4) no N1 C1 C6 C5 -179.3(2) no C2 C1 C6 C5 -1.2(4) no C1 C2 C3 C4 -1.8(4) no C2 C3 C4 N3 -174.3(4) no C2 C3 C4 C5 -0.7(4) no N3 C4 C5 C6 176.2(4) no C3 C4 C5 C6 2.3(4) no C4 C5 C6 C1 -1.4(4) no N2 C8 C12 C11 0.3(4) no C13 C8 C12 C11 -178.8(3) no N2 C8 C13 N1 0.4(3) no C12 C8 C13 N1 179.5(3) no N2 C9 C10 C11 0.3(4) no C9 C10 C11 C12 -1.2(5) no C10 C11 C12 C8 0.9(4) no