#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/03/2200319.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200319 loop_ _publ_author_name 'Zrinka Bani\'c Tomi\H-pyrrolo[2,3-d]pyrimidine-4-ylamine, an lck tyrosine kinase inhibitor ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o511 _journal_page_last o513 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C23 H22 N4 O' _chemical_formula_moiety 'C23 H22 N4 O' _chemical_formula_sum 'C23 H22 N4 O' _chemical_formula_weight 370.45 _chemical_name_systematic ; 7-Cyclopentyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-ylamine ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 11.914(2) _cell_length_b 12.399(5) _cell_length_c 26.133(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 10.55 _cell_measurement_theta_min 3.11 _cell_volume 3860.4(18) _computing_cell_refinement 'SET4 and CELDIM in CAD-4 Software' _computing_data_collection 'EXPRESS in CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .996 _diffrn_measured_fraction_theta_max .996 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .5855 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3910 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 26.31 _diffrn_reflns_theta_max 26.31 _diffrn_reflns_theta_min 2.31 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .081 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1568 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .16 _exptl_crystal_size_min .15 _refine_diff_density_max .203 _refine_diff_density_min -.229 _refine_ls_abs_structure_details none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .841 _refine_ls_hydrogen_treatment 'see text ' _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 253 _refine_ls_number_reflns 3910 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .841 _refine_ls_R_factor_all .4675 _refine_ls_R_factor_gt .0614 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0182P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1360 _reflns_number_gt 819 _reflns_number_total 3910 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na6079.cif _[local]_cod_data_source_block plr _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2200319 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,y,1/2-z 1/2-x,1/2+y,z x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O16 .093(4) .080(3) .045(3) .044(3) -.003(3) .006(3) N1 .036(3) .039(3) .042(3) .003(3) -.002(3) -.006(3) N3 .043(3) .032(3) .057(3) .000(3) -.017(3) .000(3) N7 .043(3) .027(3) .060(4) .003(3) -.011(3) -.004(3) N41 .054(4) .029(3) .069(4) -.007(3) -.016(3) -.003(3) C2 .042(4) .051(4) .053(4) .006(4) -.008(4) .001(4) C4 .045(4) .028(4) .033(4) -.005(4) .011(3) .002(3) C5 .047(5) .033(4) .034(4) .003(4) .002(3) .003(4) C6 .031(4) .052(5) .046(4) -.007(4) -.006(3) -.009(4) C8 .039(4) .033(4) .038(4) -.011(4) .001(4) .000(4) C9 .038(4) .029(4) .031(4) -.004(4) .002(3) -.004(3) C10 .033(4) .040(4) .033(4) -.005(4) .001(3) .001(4) C11 .031(4) .048(4) .044(4) .005(3) -.007(3) .007(4) C12 .046(4) .050(4) .031(4) .003(4) .005(4) -.008(4) C13 .044(5) .051(5) .046(5) .007(4) .001(4) .000(4) C14 .058(5) .063(5) .038(4) .014(4) -.001(4) -.009(4) C15 .044(5) .044(4) .054(5) .016(4) .004(4) -.008(4) C17 .060(6) .042(4) .042(5) .025(4) .005(5) .010(4) C18 .058(5) .077(6) .053(5) .001(5) .000(4) .004(5) C19 .063(6) .084(6) .072(6) .000(5) .023(5) .027(5) C20 .063(6) .095(6) .055(5) .037(5) -.007(5) .015(5) C21 .077(7) .106(7) .066(6) -.013(5) -.005(5) .002(6) C22 .086(7) .084(6) .062(6) -.024(5) .010(5) .013(5) C71 .053(5) .031(4) .068(5) -.001(4) -.012(4) -.003(4) C72 .113(7) .046(5) .076(6) -.008(5) .033(6) -.020(4) C73 .099(7) .079(6) .100(7) .020(5) -.038(6) -.030(6) C74 .091(6) .065(6) .129(8) -.027(5) .006(6) -.033(6) C75 .071(5) .047(4) .070(5) -.016(4) .009(5) -.001(4) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol O16 .2541(4) -.1436(4) .68577(16) .0727(19) Uani 1.000 O N1 -.2088(4) .3298(3) .52631(17) .0390(17) Uani 1.000 N N3 -.2389(4) .1407(4) .51220(18) .0440(17) Uani 1.000 N N7 -.0508(4) .3681(4) .58142(18) .0433(19) Uani 1.000 N N41 -.1340(4) .0086(3) .54859(15) .051(2) Uani 1.000 N C2 -.2611(4) .2454(5) .5062(2) .049(2) Uani 1.000 C C4 -.1503(5) .1147(5) .5410(2) .035(2) Uani 1.000 C C5 .0086(5) .2000(5) .5984(2) .038(3) Uani 1.000 C C6 .0265(4) .3071(5) .6072(2) .043(3) Uani 1.000 C C8 -.1191(5) .2997(5) .5546(2) .037(2) Uani 1.000 C C9 -.0834(5) .1944(5) .5634(2) .033(2) Uani 1.000 C C10 .0740(5) .1104(5) .6210(2) .035(2) Uani 1.000 C C11 .1189(4) .0271(4) .5922(2) .041(2) Uani 1.000 C C12 .1759(4) -.0555(5) .6151(2) .042(2) Uani 1.000 C C13 .1929(5) -.0577(5) .6675(3) .047(3) Uani 1.000 C C14 .1537(5) .0264(5) .6967(2) .053(3) Uani 1.000 C C15 .0930(5) .1086(4) .6737(2) .047(3) Uani 1.000 C C17 .2673(6) -.1556(5) .7384(3) .048(3) Uani 1.000 C C18 .2003(6) -.2244(6) .7635(3) .063(3) Uani 1.000 C C19 .2193(6) -.2440(6) .8148(3) .073(3) Uani 1.000 C C20 .3041(7) -.1921(6) .8393(3) .071(3) Uani 1.000 C C21 .3716(6) -.1223(6) .8139(3) .083(4) Uani 1.000 C C22 .3536(7) -.1054(6) .7630(3) .077(4) Uani 1.000 C C71 -.0632(5) .4861(4) .5846(2) .051(3) Uani 1.000 C C72 -.0838(6) .5261(5) .6392(2) .078(3) Uani 1.000 C C73 .0152(7) .5947(6) .6527(3) .093(4) Uani 1.000 C C74 .0557(6) .6381(6) .6025(3) .095(4) Uani 1.000 C C75 .0411(5) .5452(5) .5660(2) .063(3) Uani 1.000 C H2 -.32160 .26140 .48500 .0580 Uiso 1.000 H H6 .08320 .33470 .62790 .0520 Uiso 1.000 H H11 .11000 .02730 .55690 .0490 Uiso 1.000 H H12 .20390 -.11140 .59500 .0510 Uiso 1.000 H H14 .16790 .02830 .73170 .0640 Uiso 1.000 H H15 .06410 .16380 .69390 .0570 Uiso 1.000 H H18 .14160 -.25860 .74660 .0750 Uiso 1.000 H H19 .17430 -.29260 .83250 .0870 Uiso 1.000 H H20 .31600 -.20450 .87390 .0860 Uiso 1.000 H H21 .42910 -.08650 .83090 .1000 Uiso 1.000 H H22 .40070 -.05930 .74490 .0930 Uiso 1.000 H H41A -.17920 -.03740 .53520 .0600 Uiso 1.000 H H41B -.07830 -.01310 .56680 .0600 Uiso 1.000 H H71 -.12690 .50780 .56320 .0600 Uiso 1.000 H H72A -.15250 .56790 .64090 .0940 Uiso 1.000 H H72B -.08990 .46570 .66260 .0940 Uiso 1.000 H H73A .07310 .55210 .66910 .1110 Uiso 1.000 H H73B -.00670 .65280 .67540 .1110 Uiso 1.000 H H74A .13380 .65970 .60460 .1140 Uiso 1.000 H H74B .01120 .69970 .59180 .1140 Uiso 1.000 H H75A .10610 .49810 .56690 .0750 Uiso 1.000 H H75B .03080 .57110 .53130 .0750 Uiso 1.000 H loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O16 C13 . . 1.376(8) no O16 C17 . . 1.392(9) no N1 C2 . . 1.326(7) no N1 C8 . . 1.352(7) no N3 C2 . . 1.334(8) no N3 C4 . . 1.336(7) no N7 C6 . . 1.369(7) no N7 C8 . . 1.368(8) no N7 C71 . . 1.473(7) no N41 C4 . . 1.345(7) no N41 H41A . . .8589 no N41 H41B . . .8598 no C4 C9 . . 1.398(8) no C5 C9 . . 1.429(8) no C5 C10 . . 1.480(8) no C5 C6 . . 1.364(9) no C8 C9 . . 1.392(9) no C10 C15 . . 1.396(7) no C10 C11 . . 1.385(8) no C11 C12 . . 1.367(8) no C12 C13 . . 1.385(9) no C13 C14 . . 1.374(9) no C14 C15 . . 1.387(8) no C17 C18 . . 1.340(10) no C17 C22 . . 1.363(11) no C18 C19 . . 1.381(11) no C19 C20 . . 1.358(11) no C20 C21 . . 1.355(11) no C21 C22 . . 1.364(11) no C71 C75 . . 1.522(8) no C71 C72 . . 1.530(8) no C72 C73 . . 1.496(11) no C73 C74 . . 1.498(11) no C74 C75 . . 1.506(10) no C2 H2 . . .9305 no C6 H6 . . .9306 no C11 H11 . . .9286 no C12 H12 . . .9314 no C14 H14 . . .9305 no C15 H15 . . .9304 no C18 H18 . . .9295 no C19 H19 . . .9298 no C20 H20 . . .9281 no C21 H21 . . .9294 no C22 H22 . . .9302 no C71 H71 . . .9804 no C72 H72A . . .9698 no C72 H72B . . .9696 no C73 H73A . . .9688 no C73 H73B . . .9690 no C74 H74A . . .9698 no C74 H74B . . .9709 no C75 H75A . . .9702 no C75 H75B . . .9698 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -5 -2 18 5 -2 -8 0 -6 9 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 C13 O16 C17 119.0(5) no C2 N1 C8 111.7(4) no C2 N3 C4 117.2(5) no C6 N7 C8 108.0(5) no C6 N7 C71 126.1(5) no C8 N7 C71 125.8(5) no H41A N41 H41B 120.11 no C4 N41 H41A 119.94 no C4 N41 H41B 119.96 no N1 C2 N3 128.9(5) no N41 C4 C9 123.2(5) no N3 C4 N41 115.7(5) no N3 C4 C9 121.1(6) no C6 C5 C9 106.0(5) no C6 C5 C10 125.5(5) no C9 C5 C10 128.5(5) no N7 C6 C5 110.5(5) no N7 C8 C9 108.4(5) no N1 C8 C9 126.2(5) no N1 C8 N7 125.4(5) no C5 C9 C8 107.1(5) no C4 C9 C8 114.8(5) no C4 C9 C5 137.7(6) no C5 C10 C11 123.1(5) no C5 C10 C15 119.4(5) no C11 C10 C15 117.5(5) no C10 C11 C12 120.8(5) no C11 C12 C13 121.4(5) no O16 C13 C14 125.1(6) no O16 C13 C12 115.8(6) no C12 C13 C14 119.0(6) no C13 C14 C15 119.6(5) no C10 C15 C14 121.6(5) no C18 C17 C22 120.6(7) no O16 C17 C18 119.0(6) no O16 C17 C22 120.2(6) no C17 C18 C19 119.3(7) no C18 C19 C20 119.7(7) no C19 C20 C21 120.9(7) no C20 C21 C22 118.9(7) no C17 C22 C21 120.6(7) no C72 C71 C75 105.8(5) no N7 C71 C72 113.0(4) no N7 C71 C75 112.2(5) no C71 C72 C73 106.1(5) no C72 C73 C74 104.6(6) no C73 C74 C75 104.1(6) no C71 C75 C74 105.1(5) no N1 C2 H2 115.57 no N3 C2 H2 115.53 no N7 C6 H6 124.84 no C5 C6 H6 124.70 no C10 C11 H11 119.58 no C12 C11 H11 119.58 no C11 C12 H12 119.25 no C13 C12 H12 119.39 no C13 C14 H14 120.22 no C15 C14 H14 120.15 no C10 C15 H15 119.21 no C14 C15 H15 119.19 no C17 C18 H18 120.40 no C19 C18 H18 120.28 no C18 C19 H19 120.16 no C20 C19 H19 120.10 no C19 C20 H20 119.63 no C21 C20 H20 119.50 no C20 C21 H21 120.55 no C22 C21 H21 120.59 no C17 C22 H22 119.72 no C21 C22 H22 119.71 no N7 C71 H71 108.55 no C72 C71 H71 108.59 no C75 C71 H71 108.52 no C71 C72 H72A 110.56 no C71 C72 H72B 110.47 no C73 C72 H72A 110.53 no C73 C72 H72B 110.45 no H72A C72 H72B 108.70 no C72 C73 H73A 110.83 no C72 C73 H73B 110.77 no C74 C73 H73A 110.73 no C74 C73 H73B 110.85 no H73A C73 H73B 109.04 no C73 C74 H74A 111.02 no C73 C74 H74B 111.04 no C75 C74 H74A 110.98 no C75 C74 H74B 110.87 no H74A C74 H74B 108.84 no C71 C75 H75A 110.74 no C71 C75 H75B 110.77 no C74 C75 H75A 110.67 no C74 C75 H75B 110.71 no H75A C75 H75B 108.84 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O16 C6 3.380(7) 7_545 no O16 H6 2.4732 7_545 no N1 N41 2.960(6) 7_455 no N41 C11 3.230(7) . no N41 C10 3.364(7) . no N41 N1 2.960(6) 7_445 no N1 H75B 2.8764 5_566 no N1 H20 2.9347 4_556 no N1 H71 2.5985 . no N1 H41A 2.1321 7_455 no N3 H71 2.6548 7_445 no N3 H12 2.8555 5_556 no N41 H11 2.9243 . no N41 H11 2.8071 5_556 no N41 H71 2.8741 7_445 no C6 O16 3.380(7) 7_555 no C8 C20 3.543(10) 4_556 no C10 N41 3.364(7) . no C11 N41 3.230(7) . no C14 C22 3.368(10) . no C20 C8 3.543(10) 4_546 no C22 C14 3.368(10) . no C2 H41A 2.8867 7_455 no C4 H71 3.0232 7_445 no C5 H41B 2.9555 . no C5 H19 2.8315 4_556 no C5 H2 3.0119 3_556 no C6 H75A 2.7599 . no C6 H15 2.9140 . no C6 H72B 2.8082 . no C8 H20 2.9995 4_556 no C8 H75B 2.9516 5_566 no C9 H19 2.9325 4_556 no C10 H41B 2.7647 . no C11 H41B 2.4918 . no C12 H75A 2.9621 7_545 no C15 H6 3.0505 . no C17 H14 2.5753 . no C19 H72B 3.0799 4_546 no C19 H72A 3.0187 6_546 no C20 H72A 3.0644 6_546 no C20 H73B 2.9878 6_546 no C22 H14 2.8831 . no C75 H75B 3.0461 5_566 no H2 C5 3.0119 3_456 no H6 C15 3.0505 . no H6 H75A 2.5924 . no H6 O16 2.4732 7_555 no H11 N41 2.9243 . no H11 H41B 2.3132 . no H11 N41 2.8071 5_556 no H11 H41A 2.5472 5_556 no H12 N3 2.8555 5_556 no H14 C17 2.5753 . no H14 C22 2.8831 . no H15 C6 2.9140 . no H19 C5 2.8315 4_546 no H19 C9 2.9325 4_546 no H20 N1 2.9347 4_546 no H20 C8 2.9995 4_546 no H22 H73A 2.4350 7_545 no H41A H11 2.5472 5_556 no H41A N1 2.1321 7_445 no H41A C2 2.8867 7_445 no H41A H71 2.4872 7_445 no H41B C5 2.9555 . no H41B C10 2.7647 . no H41B C11 2.4918 . no H41B H11 2.3132 . no H71 N1 2.5985 . no H71 N3 2.6548 7_455 no H71 N41 2.8741 7_455 no H71 C4 3.0232 7_455 no H71 H41A 2.4872 7_455 no H72A C19 3.0187 6_466 no H72A C20 3.0644 6_466 no H72B C6 2.8082 . no H72B C19 3.0799 4_556 no H73A H22 2.4350 7_555 no H73B C20 2.9878 6_466 no H75A C6 2.7599 . no H75A H6 2.5924 . no H75A C12 2.9621 7_555 no H75B N1 2.8764 5_566 no H75B C8 2.9516 5_566 no H75B C75 3.0461 5_566 no H75B H75B 2.5147 5_566 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N41 H41A N1 7_445 .86 2.13 2.960(6) 162 yes C6 H6 O16 7_555 .93 2.47 3.380(7) 165 yes C71 H71 N1 . .98 2.60 3.014(7) 106 yes 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 N1 C8 C9 C5 -175.5(5) yes N7 C8 C9 C4 176.0(5) yes C6 C5 C10 C11 -130.1(6) yes C6 C5 C10 C15 49.4(8) yes C9 C5 C10 C11 49.3(9) yes C9 C5 C10 C15 -131.2(6) yes C12 C13 O16 C17 -175.2(5) yes C14 C13 O16 C17 8.3(9) yes C13 O16 C17 C18 98.4(7) yes C13 O16 C17 C22 -87.4(8) yes C6 N7 C71 C72 -57.3(7) yes C6 N7 C71 C75 62.2(7) yes C8 N7 C71 C72 118.3(6) yes C8 N7 C71 C75 -122.1(6) yes C2 N1 C8 C9 -.9(8) no C8 N1 C2 N3 2.9(8) no C2 N1 C8 N7 -177.8(5) no C4 N3 C2 N1 -2.2(8) no C2 N3 C4 C9 -.6(8) no C2 N3 C4 N41 176.4(5) no C8 N7 C6 C5 -1.1(6) no C71 N7 C6 C5 175.2(5) no C6 N7 C8 N1 176.8(5) no C6 N7 C8 C9 -.5(6) no C71 N7 C8 N1 .5(9) no C71 N7 C8 C9 -176.8(5) no N3 C4 C9 C8 2.1(8) no N41 C4 C9 C5 -3.0(11) no N41 C4 C9 C8 -174.7(5) no N3 C4 C9 C5 173.8(6) no C6 C5 C9 C4 -174.5(7) no C10 C5 C6 N7 -178.4(5) no C6 C5 C9 C8 -2.4(6) no C10 C5 C9 C4 6.0(11) no C9 C5 C6 N7 2.1(6) no C10 C5 C9 C8 178.1(5) no N1 C8 C9 C4 -1.3(8) no N7 C8 C9 C5 1.8(6) no C15 C10 C11 C12 2.4(8) no C5 C10 C15 C14 180.0(9) no C5 C10 C11 C12 -178.1(5) no C11 C10 C15 C14 -.5(9) no C10 C11 C12 C13 -1.4(8) no C11 C12 C13 O16 -178.3(5) no C11 C12 C13 C14 -1.5(9) no C12 C13 C14 C15 3.4(9) no O16 C13 C14 C15 179.9(7) no C13 C14 C15 C10 -2.4(9) no O16 C17 C22 C21 -175.7(7) no C18 C17 C22 C21 -1.6(11) no O16 C17 C18 C19 174.3(6) no C22 C17 C18 C19 .1(12) no C17 C18 C19 C20 1.1(11) no C18 C19 C20 C21 -1.0(12) no C19 C20 C21 C22 -.5(12) no C20 C21 C22 C17 1.8(11) no N7 C71 C75 C74 -140.1(5) no C72 C71 C75 C74 -16.4(6) no N7 C71 C72 C73 116.2(6) no C75 C71 C72 C73 -7.0(6) no C71 C72 C73 C74 27.9(7) no C72 C73 C74 C75 -38.3(7) no C73 C74 C75 C71 33.8(7) no _journal_paper_doi 10.1107/S1600536801007917