# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name D.Millar H.Maynard-Casely D.Allan A.Cumming A.Lennie A.Mackay ; Iain D.H.Oswald ; C.Tang 'Colin R.Pulham' _publ_contact_author_name 'David Millar' _publ_contact_author_email d.i.a.millar@sms.ed.ac.uk # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # data_1 _database_code_depnum_ccdc_archive 'CCDC 832144' #TrackingRef '- cl20dmf.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 7.7843(16) _cell_length_b 12.857(3) _cell_length_c 13.002(3) _cell_angle_alpha 113.73(3) _cell_angle_beta 106.34(3) _cell_angle_gamma 92.43(3) _cell_volume 1125.1(6) _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' 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 2 # Given Formula = C9 H13 N13 O13 # Dc = 1.51 Fooo = 604.00 Mu = 1.40 M = 511.28 # Found Formula = C12 H20 N14 O14 # Dc = 1.72 FOOO = 604.00 Mu = 1.56 M = 584.38 _chemical_formula_sum 'C12 H20 N14 O14' _chemical_formula_moiety 'C12 H20 N14 O14' _chemical_compound_source ? _chemical_formula_weight 584.38 _cell_measurement_reflns_used 4391 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.156 # Sheldrick geometric approximatio 0.97 0.97 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'd*TREK (Pflugrath, 1999)' _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 0.46 _diffrn_measurement_device 'Rigaku Saturn' _diffrn_measurement_device_type CCD _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 13119 _reflns_number_total 6199 _diffrn_reflns_av_R_equivalents 0.127 # Number of reflections without Friedels Law is 6199 # Number of reflections with Friedels Law is 0 # Theoretical number of reflections is about 6963 _diffrn_reflns_theta_min 2.686 _diffrn_reflns_theta_max 29.621 _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 25.771 _diffrn_measured_fraction_theta_full 0.911 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -18 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 0.42 _oxford_diffrn_Wilson_scale 0.56 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.46 _refine_diff_density_max 0.48 # 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>-10.0\s(I) _refine_ls_number_reflns 6175 _refine_ls_number_restraints 0 _refine_ls_number_parameters 362 _oxford_refine_ls_R_factor_ref 0.0645 _refine_ls_wR_factor_ref 0.1639 _refine_ls_goodness_of_fit_ref 1.0250 _refine_ls_shift/su_max 0.0004954 _refine_ls_shift/su_mean 0.0369298 # The values computed from all data _oxford_reflns_number_all 6175 _refine_ls_R_factor_all 0.0645 _refine_ls_wR_factor_all 0.1639 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5775 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_gt 0.1601 # 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 none # 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^) + ( 0.11P)^2^ + 0.46P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 C1 C 0.29282(16) 0.21076(9) 0.63183(9) 0.0119 1.0000 Uani . . . . . . . C2 C 0.47437(15) 0.36651(8) 0.63756(9) 0.0095 1.0000 Uani . . . . . . . C3 C 0.52167(16) 0.24936(9) 0.55854(9) 0.0108 1.0000 Uani . . . . . . . C4 C 0.11577(16) 0.19157(9) 0.52328(9) 0.0116 1.0000 Uani . . . . . . . C5 C 0.20465(15) 0.33913(9) 0.46949(9) 0.0098 1.0000 Uani . . . . . . . C6 C 0.25034(15) 0.22120(9) 0.39184(9) 0.0103 1.0000 Uani . . . . . . . N7 N 0.36111(14) 0.33346(8) 0.69518(8) 0.0110 1.0000 Uani . . . . . . . N8 N 0.40665(15) 0.38884(9) 0.81829(9) 0.0154 1.0000 Uani . . . . . . . N9 N 0.43390(14) 0.16427(8) 0.58407(9) 0.0127 1.0000 Uani . . . . . . . N10 N 0.54612(17) 0.10399(8) 0.63451(9) 0.0182 1.0000 Uani . . . . . . . N11 N 0.15362(14) 0.13701(8) 0.41382(8) 0.0124 1.0000 Uani . . . . . . . N12 N 0.04388(15) 0.03768(8) 0.32276(9) 0.0148 1.0000 Uani . . . . . . . N13 N 0.07992(14) 0.30035(8) 0.51824(8) 0.0110 1.0000 Uani . . . . . . . N14 N 0.03335(14) 0.38036(9) 0.60878(9) 0.0145 1.0000 Uani . . . . . . . N15 N 0.37097(13) 0.41139(7) 0.55923(8) 0.0103 1.0000 Uani . . . . . . . N16 N 0.39968(15) 0.52886(8) 0.59187(9) 0.0133 1.0000 Uani . . . . . . . N17 N 0.44331(14) 0.22733(8) 0.43615(8) 0.0115 1.0000 Uani . . . . . . . N18 N 0.53713(15) 0.17670(8) 0.35719(9) 0.0136 1.0000 Uani . . . . . . . O19 O 0.34776(17) 0.33688(9) 0.86442(9) 0.0257 1.0000 Uani . . . . . . . O20 O 0.49007(15) 0.48653(8) 0.86547(8) 0.0217 1.0000 Uani . . . . . . . O21 O 0.49288(17) 0.06746(9) 0.69472(10) 0.0285 1.0000 Uani . . . . . . . O22 O 0.68170(15) 0.08661(8) 0.60630(9) 0.0241 1.0000 Uani . . . . . . . O23 O 0.06170(14) 0.48033(8) 0.62532(9) 0.0191 1.0000 Uani . . . . . . . O24 O -0.03559(14) 0.34313(9) 0.66351(9) 0.0215 1.0000 Uani . . . . . . . O25 O -0.05535(15) -0.01643(8) 0.34842(10) 0.0236 1.0000 Uani . . . . . . . O26 O 0.06387(16) 0.00942(8) 0.22629(8) 0.0226 1.0000 Uani . . . . . . . O27 O 0.52636(15) 0.58767(8) 0.68138(9) 0.0236 1.0000 Uani . . . . . . . O28 O 0.30319(14) 0.56274(8) 0.52540(9) 0.0205 1.0000 Uani . . . . . . . O29 O 0.69427(14) 0.17105(9) 0.40025(9) 0.0210 1.0000 Uani . . . . . . . O30 O 0.45502(15) 0.14690(8) 0.25288(8) 0.0204 1.0000 Uani . . . . . . . O31 O 0.92967(17) 0.23558(11) 0.23721(10) 0.0329 1.0000 Uani . . . . . . . C32 C 0.7778(2) 0.23345(12) 0.17758(12) 0.0219 1.0000 Uani . . . . . . . N33 N 0.69808(18) 0.16268(13) 0.06358(11) 0.0260 1.0000 Uani . . . . . . . C34 C 0.7904(3) 0.07794(16) -0.00005(17) 0.0442 1.0000 Uani . . . . . . . C35 C 0.5222(3) 0.1715(4) -0.0030(3) 0.0688 1.0000 Uani . . . . . . . C36 C 1.1180(2) 0.3033(2) 1.03140(18) 0.0387 1.0000 Uani . . . . . . . N37 N 0.95008(17) 0.33562(11) 0.98091(10) 0.0214 1.0000 Uani . . . . . . . C38 C 0.8832(3) 0.42653(14) 1.05951(13) 0.0346 1.0000 Uani . . . . . . . C39 C 0.86511(19) 0.28699(11) 0.86414(11) 0.0189 1.0000 Uani . . . . . . . O40 O 0.72543(14) 0.31140(9) 0.81391(9) 0.0221 1.0000 Uani . . . . . . . H11 H 0.2675 0.1793 0.6843 0.0125 1.0000 Uiso R . . . . . . H21 H 0.5847 0.4207 0.6956 0.0092 1.0000 Uiso R . . . . . . H31 H 0.6515 0.2506 0.5769 0.0130 1.0000 Uiso R . . . . . . H41 H 0.0087 0.1496 0.5254 0.0102 1.0000 Uiso R . . . . . . H51 H 0.1418 0.3767 0.4201 0.0109 1.0000 Uiso R . . . . . . H61 H 0.2091 0.2022 0.3070 0.0155 1.0000 Uiso R . . . . . . H321 H 0.7104 0.2845 0.2151 0.0262 1.0000 Uiso R . . . . . . H341 H 0.7140 0.0033 -0.0319 0.0488 1.0000 Uiso R . . . . . . H342 H 0.8082 0.0935 -0.0627 0.0485 1.0000 Uiso R . . . . . . H343 H 0.9052 0.0792 0.0554 0.0490 1.0000 Uiso R . . . . . . H351 H 0.4433 0.0975 -0.0369 0.0777 1.0000 Uiso R . . . . . . H352 H 0.5316 0.1902 -0.0661 0.0777 1.0000 Uiso R . . . . . . H353 H 0.4718 0.2299 0.0471 0.0779 1.0000 Uiso R . . . . . . H361 H 1.1242 0.2269 0.9785 0.0457 1.0000 Uiso R . . . . . . H362 H 1.1189 0.3072 1.1064 0.0459 1.0000 Uiso R . . . . . . H363 H 1.2192 0.3565 1.0426 0.0460 1.0000 Uiso R . . . . . . H381 H 0.7577 0.4214 1.0238 0.0413 1.0000 Uiso R . . . . . . H382 H 0.9043 0.4213 1.1338 0.0406 1.0000 Uiso R . . . . . . H383 H 0.9487 0.4992 1.0759 0.0418 1.0000 Uiso R . . . . . . H391 H 0.9148 0.2291 0.8161 0.0189 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 C1 0.0177(5) 0.0067(4) 0.0073(4) 0.0017(3) 0.0008(4) -0.0021(3) C2 0.0119(5) 0.0064(4) 0.0070(4) 0.0011(3) 0.0015(3) 0.0004(3) C3 0.0143(5) 0.0064(4) 0.0074(4) 0.0004(3) 0.0009(3) 0.0015(3) C4 0.0151(5) 0.0074(4) 0.0083(4) 0.0016(3) 0.0012(4) -0.0022(3) C5 0.0120(5) 0.0068(4) 0.0080(4) 0.0020(3) 0.0014(3) 0.0000(3) C6 0.0134(5) 0.0063(4) 0.0077(4) 0.0009(3) 0.0017(3) -0.0003(3) N7 0.0165(5) 0.0069(4) 0.0042(4) -0.0006(3) 0.0008(3) -0.0023(3) N8 0.0205(5) 0.0131(4) 0.0069(4) 0.0003(3) 0.0027(3) 0.0007(4) N9 0.0174(5) 0.0072(4) 0.0109(4) 0.0042(3) 0.0004(3) 0.0021(3) N10 0.0258(6) 0.0063(4) 0.0132(4) 0.0022(3) -0.0041(4) 0.0017(4) N11 0.0171(5) 0.0070(4) 0.0060(4) -0.0013(3) 0.0004(3) -0.0049(3) N12 0.0167(5) 0.0053(4) 0.0127(4) -0.0015(3) -0.0010(3) -0.0005(3) N13 0.0131(5) 0.0082(4) 0.0092(4) 0.0018(3) 0.0030(3) 0.0006(3) N14 0.0128(5) 0.0150(4) 0.0110(4) 0.0018(3) 0.0029(3) 0.0015(3) N15 0.0141(5) 0.0031(3) 0.0103(4) 0.0017(3) 0.0014(3) -0.0006(3) N16 0.0184(5) 0.0046(4) 0.0155(4) 0.0027(3) 0.0063(4) 0.0002(3) N17 0.0142(5) 0.0108(4) 0.0065(4) 0.0010(3) 0.0032(3) 0.0025(3) N18 0.0198(5) 0.0073(4) 0.0123(4) 0.0011(3) 0.0077(4) 0.0008(3) O19 0.0401(6) 0.0236(5) 0.0111(4) 0.0058(4) 0.0086(4) -0.0037(4) O20 0.0302(5) 0.0116(4) 0.0117(4) -0.0042(3) 0.0049(3) -0.0037(3) O21 0.0374(6) 0.0205(5) 0.0285(5) 0.0189(4) 0.0003(4) 0.0009(4) O22 0.0289(5) 0.0142(4) 0.0203(4) 0.0028(3) 0.0011(4) 0.0119(4) O23 0.0222(5) 0.0121(4) 0.0204(4) 0.0040(3) 0.0073(3) 0.0061(3) O24 0.0227(5) 0.0233(5) 0.0165(4) 0.0045(4) 0.0103(3) -0.0020(4) O25 0.0247(5) 0.0101(4) 0.0264(5) -0.0002(3) 0.0081(4) -0.0069(3) O26 0.0340(6) 0.0125(4) 0.0107(4) -0.0030(3) 0.0042(4) 0.0003(4) O27 0.0305(6) 0.0067(4) 0.0200(5) 0.0001(3) -0.0020(4) -0.0049(3) O28 0.0238(5) 0.0124(4) 0.0282(5) 0.0135(4) 0.0054(4) 0.0042(3) O29 0.0175(5) 0.0190(4) 0.0218(4) 0.0029(4) 0.0083(3) 0.0049(3) O30 0.0296(5) 0.0189(4) 0.0097(4) 0.0022(3) 0.0081(3) 0.0034(4) O31 0.0304(6) 0.0314(6) 0.0202(5) 0.0042(4) -0.0058(4) 0.0062(5) C32 0.0256(7) 0.0233(6) 0.0167(6) 0.0082(5) 0.0074(5) 0.0077(5) N33 0.0234(6) 0.0354(7) 0.0154(5) 0.0122(5) -0.0004(4) -0.0006(5) C34 0.0689(14) 0.0246(7) 0.0231(7) -0.0029(6) 0.0127(8) 0.0003(8) C35 0.0314(11) 0.118(3) 0.0522(14) 0.0506(16) -0.0134(10) 0.0036(13) C36 0.0232(8) 0.0603(12) 0.0352(8) 0.0314(9) -0.0022(6) 0.0030(7) N37 0.0232(6) 0.0219(5) 0.0132(5) 0.0063(4) 0.0002(4) -0.0011(4) C38 0.0616(12) 0.0212(6) 0.0153(6) 0.0021(5) 0.0131(6) 0.0038(7) C39 0.0207(6) 0.0168(5) 0.0137(5) 0.0033(4) 0.0027(4) 0.0024(4) O40 0.0229(5) 0.0197(4) 0.0154(4) 0.0036(3) 0.0002(3) 0.0042(4) _refine_ls_extinction_coef 3180.299 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.835(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 C1 . C4 . 1.5965(17) yes C1 . N7 . 1.4446(14) yes C1 . N9 . 1.4455(17) yes C1 . H11 . 0.980 no C2 . C3 . 1.5730(16) yes C2 . N7 . 1.4543(15) yes C2 . N15 . 1.4386(14) yes C2 . H21 . 0.977 no C3 . N9 . 1.4596(15) yes C3 . N17 . 1.4357(14) yes C3 . H31 . 0.969 no C4 . N11 . 1.4333(15) yes C4 . N13 . 1.4611(14) yes C4 . H41 . 0.987 no C5 . C6 . 1.5687(16) yes C5 . N13 . 1.4672(15) yes C5 . N15 . 1.4411(16) yes C5 . H51 . 0.989 no C6 . N11 . 1.4564(14) yes C6 . N17 . 1.4356(15) yes C6 . H61 . 0.979 no N7 . N8 . 1.3918(14) yes N8 . O19 . 1.2114(15) yes N8 . O20 . 1.2093(15) yes N9 . N10 . 1.3921(14) yes N10 . O21 . 1.2111(16) yes N10 . O22 . 1.2125(18) yes N11 . N12 . 1.3727(15) yes N12 . O25 . 1.2158(15) yes N12 . O26 . 1.2155(15) yes N13 . N14 . 1.3684(14) yes N14 . O23 . 1.2140(14) yes N14 . O24 . 1.2209(14) yes N15 . N16 . 1.3832(13) yes N16 . O27 . 1.2172(15) yes N16 . O28 . 1.2110(14) yes N17 . N18 . 1.3912(14) yes N18 . O29 . 1.2124(16) yes N18 . O30 . 1.2117(14) yes O31 . C32 . 1.2100(19) yes C32 . N33 . 1.3264(19) yes C32 . H321 . 0.927 no N33 . C34 . 1.436(3) yes N33 . C35 . 1.436(3) yes C34 . H341 . 0.969 no C34 . H342 . 0.957 no C34 . H343 . 0.972 no C35 . H351 . 0.967 no C35 . H352 . 0.964 no C35 . H353 . 0.958 no C36 . N37 . 1.448(2) yes C36 . H361 . 0.958 no C36 . H362 . 0.954 no C36 . H363 . 0.959 no N37 . C38 . 1.439(2) yes N37 . C39 . 1.3303(17) yes C38 . H381 . 0.943 no C38 . H382 . 0.964 no C38 . H383 . 0.958 no C39 . O40 . 1.2255(17) yes C39 . H391 . 0.938 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 C4 . C1 . N7 . 107.11(10) yes C4 . C1 . N9 . 108.15(9) yes N7 . C1 . N9 . 103.85(10) yes C4 . C1 . H11 . 112.3 no N7 . C1 . H11 . 111.3 no N9 . C1 . H11 . 113.6 no C3 . C2 . N7 . 104.12(8) yes C3 . C2 . N15 . 107.63(9) yes N7 . C2 . N15 . 110.21(9) yes C3 . C2 . H21 . 110.9 no N7 . C2 . H21 . 111.5 no N15 . C2 . H21 . 112.1 no C2 . C3 . N9 . 103.75(9) yes C2 . C3 . N17 . 108.31(9) yes N9 . C3 . N17 . 110.96(9) yes C2 . C3 . H31 . 112.6 no N9 . C3 . H31 . 111.9 no N17 . C3 . H31 . 109.2 no C1 . C4 . N11 . 109.49(10) yes C1 . C4 . N13 . 111.70(9) yes N11 . C4 . N13 . 98.78(9) yes C1 . C4 . H41 . 111.5 no N11 . C4 . H41 . 113.4 no N13 . C4 . H41 . 111.3 no C6 . C5 . N13 . 101.00(8) yes C6 . C5 . N15 . 108.49(10) yes N13 . C5 . N15 . 113.12(9) yes C6 . C5 . H51 . 111.5 no N13 . C5 . H51 . 110.3 no N15 . C5 . H51 . 112.0 no C5 . C6 . N11 . 103.81(9) yes C5 . C6 . N17 . 107.60(9) yes N11 . C6 . N17 . 110.64(9) yes C5 . C6 . H61 . 113.0 no N11 . C6 . H61 . 110.2 no N17 . C6 . H61 . 111.3 no C2 . N7 . C1 . 109.34(9) yes C2 . N7 . N8 . 119.56(9) yes C1 . N7 . N8 . 120.39(9) yes N7 . N8 . O19 . 116.45(11) yes N7 . N8 . O20 . 115.69(11) yes O19 . N8 . O20 . 127.65(11) yes C3 . N9 . C1 . 108.92(9) yes C3 . N9 . N10 . 117.03(10) yes C1 . N9 . N10 . 119.40(10) yes N9 . N10 . O21 . 117.22(12) yes N9 . N10 . O22 . 115.91(11) yes O21 . N10 . O22 . 126.65(12) yes C6 . N11 . C4 . 110.83(9) yes C6 . N11 . N12 . 121.90(10) yes C4 . N11 . N12 . 120.90(10) yes N11 . N12 . O25 . 116.68(11) yes N11 . N12 . O26 . 116.49(11) yes O25 . N12 . O26 . 126.67(11) yes C5 . N13 . C4 . 110.60(9) yes C5 . N13 . N14 . 119.21(9) yes C4 . N13 . N14 . 118.27(10) yes N13 . N14 . O23 . 117.09(10) yes N13 . N14 . O24 . 116.22(11) yes O23 . N14 . O24 . 126.67(11) yes C5 . N15 . C2 . 117.25(9) yes C5 . N15 . N16 . 120.13(9) yes C2 . N15 . N16 . 119.70(9) yes N15 . N16 . O27 . 116.79(11) yes N15 . N16 . O28 . 117.06(11) yes O27 . N16 . O28 . 126.02(11) yes C3 . N17 . C6 . 117.38(10) yes C3 . N17 . N18 . 119.43(10) yes C6 . N17 . N18 . 119.79(10) yes N17 . N18 . O29 . 116.66(10) yes N17 . N18 . O30 . 116.40(11) yes O29 . N18 . O30 . 126.87(11) yes O31 . C32 . N33 . 125.54(15) yes O31 . C32 . H321 . 117.3 no N33 . C32 . H321 . 117.2 no C32 . N33 . C34 . 120.72(15) yes C32 . N33 . C35 . 122.0(2) yes C34 . N33 . C35 . 117.2(2) yes N33 . C34 . H341 . 107.0 no N33 . C34 . H342 . 109.6 no H341 . C34 . H342 . 110.7 no N33 . C34 . H343 . 108.9 no H341 . C34 . H343 . 108.8 no H342 . C34 . H343 . 111.7 no N33 . C35 . H351 . 108.1 no N33 . C35 . H352 . 110.0 no H351 . C35 . H352 . 109.2 no N33 . C35 . H353 . 110.9 no H351 . C35 . H353 . 109.6 no H352 . C35 . H353 . 108.9 no N37 . C36 . H361 . 109.5 no N37 . C36 . H362 . 107.5 no H361 . C36 . H362 . 111.3 no N37 . C36 . H363 . 109.4 no H361 . C36 . H363 . 109.4 no H362 . C36 . H363 . 109.6 no C36 . N37 . C38 . 118.27(15) yes C36 . N37 . C39 . 120.82(15) yes C38 . N37 . C39 . 120.80(14) yes N37 . C38 . H381 . 109.9 no N37 . C38 . H382 . 110.3 no H381 . C38 . H382 . 109.7 no N37 . C38 . H383 . 108.6 no H381 . C38 . H383 . 110.3 no H382 . C38 . H383 . 108.0 no N37 . C39 . O40 . 125.05(13) yes N37 . C39 . H391 . 117.9 no O40 . C39 . H391 . 117.0 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 C1 . H11 . O25 2_556 133 0.98 2.43 3.181(2) yes C3 . H31 . O24 1_655 154 0.97 2.40 3.297(2) yes C34 . H342 . O26 2_655 133 0.96 2.51 3.245(2) yes # Attachment '- cl20dxn.cif' data_cl20dxn _database_code_depnum_ccdc_archive 'CCDC 832145' #TrackingRef '- cl20dxn.cif' _audit_creation_date 11-06-23 _audit_creation_method CRYSTALS_ver_12.87 _oxford_structure_analysis_title ; CL-20:dioxane (1:4) Co-crystal ; _chemical_name_systematic ; 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane: 1,4-dioxane (1:4) Co-crystal ; _chemical_melting_point ? _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 10.3061(3) _cell_length_b 10.7691(3) _cell_length_c 14.5298(4) _cell_angle_alpha 73.897(2) _cell_angle_beta 89.527(2) _cell_angle_gamma 85.057(2) _cell_volume 1543.38(8) _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' 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 = C10 H14 N12 O14 # Dc = 2.26 Fooo = 780.00 Mu = 2.11 M = 1052.59 # Found Formula = C10 H17 N6 O9.50 # Dc = 1.61 FOOO = 780.00 Mu = 1.43 M = 746.56 _chemical_formula_sum 'C10 H17 N6 O9.50' _chemical_formula_moiety 'C10 H17 N6 O9.50' _chemical_compound_source ? _chemical_formula_weight 373.28 _cell_measurement_reflns_used 4401 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.190 _exptl_crystal_size_mid 0.260 _exptl_crystal_size_max 0.370 _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.143 # Sheldrick geometric approximatio 0.96 0.97 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9635 _exptl_absorpt_correction_T_max 0.9732 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 16796 _reflns_number_total 6375 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 6375 # Theoretical number of reflections is about 12900 _diffrn_reflns_theta_min 1.459 _diffrn_reflns_theta_max 26.576 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.248 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 2.86 _oxford_diffrn_Wilson_scale 59.54 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.95 _refine_diff_density_max 1.03 # 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>-10.0\s(I) _refine_ls_number_reflns 6352 _refine_ls_number_restraints 0 _refine_ls_number_parameters 514 _oxford_refine_ls_R_factor_ref 0.0738 _refine_ls_wR_factor_ref 0.1526 _refine_ls_goodness_of_fit_ref 0.9917 _refine_ls_shift/su_max 0.0002803 _refine_ls_shift/su_mean 0.0002196 # The values computed from all data _oxford_reflns_number_all 6352 _refine_ls_R_factor_all 0.0738 _refine_ls_wR_factor_all 0.1526 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6066 _refine_ls_R_factor_gt 0.0710 _refine_ls_wR_factor_gt 0.1482 # 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 none # 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^) + ( 0.05P)^2^ + 2.74P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 1.09131(18) -0.12781(18) 1.00950(13) 0.0358 1.0000 Uani . . . . . . . N2 N 1.0196(2) -0.12690(19) 0.94270(15) 0.0287 1.0000 Uani . . . . . . . O3 O 0.90122(17) -0.11638(18) 0.94082(14) 0.0360 1.0000 Uani . . . . . . . N4 N 1.08011(19) -0.1440(2) 0.86168(14) 0.0271 1.0000 Uani . . . . . . . C5 C 1.0061(2) -0.1136(3) 0.77193(18) 0.0314 1.0000 Uani . . . . . . . N6 N 1.0990(2) -0.1706(3) 0.71591(19) 0.0454 1.0000 Uani . . . . . . . N7 N 1.0819(3) -0.3016(3) 0.7195(2) 0.0559 1.0000 Uani . . . . . . . O8 O 0.9719(2) -0.3330(2) 0.73010(17) 0.0532 1.0000 Uani . . . . . . . O9 O 1.1779(2) -0.3671(3) 0.7053(3) 0.0859 1.0000 Uani . . . . . . . C10 C 1.2315(3) -0.1465(3) 0.7429(2) 0.0416 1.0000 Uani . . . . . . . C11 C 1.2175(2) -0.1211(2) 0.84388(18) 0.0280 1.0000 Uani . . . . . . . N12 N 1.24751(19) 0.0099(2) 0.83539(14) 0.0261 1.0000 Uani . . . . . . . N13 N 1.30765(19) 0.0383(2) 0.91262(14) 0.0277 1.0000 Uani . . . . . . . O14 O 1.30944(19) 0.15212(18) 0.90822(15) 0.0405 1.0000 Uani . . . . . . . O15 O 1.35762(19) -0.05256(19) 0.97410(13) 0.0382 1.0000 Uani . . . . . . . C16 C 1.1735(2) 0.1118(3) 0.76585(18) 0.0315 1.0000 Uani . . . . . . . N17 N 1.03300(19) 0.1051(2) 0.78573(15) 0.0297 1.0000 Uani . . . . . . . C18 C 0.9798(2) 0.0362(3) 0.72326(17) 0.0336 1.0000 Uani . . . . . . . N19 N 1.0580(2) 0.0729(3) 0.63812(16) 0.0574 1.0000 Uani . . . . . . . C20 C 1.1909(3) 0.0863(4) 0.66501(19) 0.0466 1.0000 Uani . . . . . . . N21 N 1.2749(2) -0.0324(3) 0.67688(16) 0.0455 1.0000 Uani . . . . . . . N22 N 1.3335(3) -0.0518(6) 0.5930(2) 0.0837 1.0000 Uani . . . . . . . O23 O 1.3594(2) -0.1628(5) 0.5904(2) 0.1021 1.0000 Uani . . . . . . . O24 O 1.3592(3) 0.0472(5) 0.53372(19) 0.1235 1.0000 Uani . . . . . . . H25 H 1.2264 0.1600 0.6190 0.0546 1.0000 Uiso R . . . . . . N26 N 1.0075(2) 0.1275(2) 0.54980(15) 0.0347 1.0000 Uani . . . . . . . O27 O 1.0844(2) 0.1654(2) 0.48641(13) 0.0477 1.0000 Uani . . . . . . . O28 O 0.8897(2) 0.1306(3) 0.54174(16) 0.0616 1.0000 Uani . . . . . . . H29 H 0.8871 0.0608 0.7102 0.0389 1.0000 Uiso R . . . . . . N30 N 0.9629(2) 0.2247(2) 0.78732(16) 0.0356 1.0000 Uani . . . . . . . O31 O 0.84611(18) 0.2319(2) 0.77376(15) 0.0445 1.0000 Uani . . . . . . . O32 O 1.0252(2) 0.30321(19) 0.80815(16) 0.0439 1.0000 Uani . . . . . . . H33 H 1.1991 0.1955 0.7673 0.0367 1.0000 Uiso R . . . . . . H34 H 1.2754 -0.1822 0.8908 0.0330 1.0000 Uiso R . . . . . . H35 H 1.2932 -0.2219 0.7462 0.0497 1.0000 Uiso R . . . . . . H36 H 0.9259 -0.1555 0.7793 0.0366 1.0000 Uiso R . . . . . . O37 O 0.5340(2) -0.2503(3) 0.78792(16) 0.0545 1.0000 Uani . . . . . . . C38 C 0.5806(3) -0.1994(4) 0.8610(2) 0.0545 1.0000 Uani . . . . . . . C39 C 0.6100(3) -0.0618(4) 0.8196(2) 0.0551 1.0000 Uani . . . . . . . O40 O 0.70835(19) -0.0537(3) 0.74837(15) 0.0582 1.0000 Uani . . . . . . . C41 C 0.6663(3) -0.1070(4) 0.6757(2) 0.0579 1.0000 Uani . . . . . . . C42 C 0.6321(3) -0.2438(4) 0.7166(3) 0.0628 1.0000 Uani . . . . . . . H43 H 0.5993 -0.2777 0.6665 0.0725 1.0000 Uiso R . . . . . . H44 H 0.7090 -0.2976 0.7463 0.0724 1.0000 Uiso R . . . . . . H45 H 0.5914 -0.0528 0.6414 0.0696 1.0000 Uiso R . . . . . . H46 H 0.7369 -0.1068 0.6309 0.0700 1.0000 Uiso R . . . . . . H47 H 0.6424 -0.0283 0.8697 0.0655 1.0000 Uiso R . . . . . . H48 H 0.5326 -0.0090 0.7898 0.0655 1.0000 Uiso R . . . . . . H49 H 0.6602 -0.2497 0.8905 0.0649 1.0000 Uiso R . . . . . . H50 H 0.5139 -0.2011 0.9081 0.0645 1.0000 Uiso R . . . . . . O51 O 0.8434(2) -0.4217(2) 0.9527(2) 0.0601 1.0000 Uani . . . . . . . C52 C 0.8411(3) -0.5344(3) 0.9200(3) 0.0603 1.0000 Uani . . . . . . . C53 C 0.7087(3) -0.5849(3) 0.9333(3) 0.0612 1.0000 Uani . . . . . . . O54 O 0.6719(2) -0.6147(2) 1.0314(2) 0.0581 1.0000 Uani . . . . . . . C55 C 0.6744(3) -0.5024(3) 1.0651(3) 0.0610 1.0000 Uani . . . . . . . C56 C 0.8070(3) -0.4504(3) 1.0500(3) 0.0649 1.0000 Uani . . . . . . . H57 H 0.8716 -0.5164 1.0880 0.0755 1.0000 Uiso R . . . . . . H58 H 0.8052 -0.3724 1.0705 0.0759 1.0000 Uiso R . . . . . . H59 H 0.6084 -0.4368 1.0284 0.0714 1.0000 Uiso R . . . . . . H60 H 0.6513 -0.5248 1.1323 0.0718 1.0000 Uiso R . . . . . . H61 H 0.6441 -0.5198 0.8952 0.0721 1.0000 Uiso R . . . . . . H62 H 0.7094 -0.6633 0.9120 0.0721 1.0000 Uiso R . . . . . . H63 H 0.9052 -0.6001 0.9567 0.0718 1.0000 Uiso R . . . . . . H64 H 0.8649 -0.5121 0.8525 0.0720 1.0000 Uiso R . . . . . . H65 H 1.1428 0.5746 0.3809 0.0588 1.0000 Uiso R . . . . . . C66 C 1.0764(3) 0.5251(3) 0.4194(2) 0.0493 1.0000 Uani . . . . . . . O67 O 0.9666(2) 0.6127(2) 0.42314(16) 0.0510 1.0000 Uani . . . . . . . C68 C 0.8708(3) 0.5415(3) 0.4818(2) 0.0531 1.0000 Uani . . . . . . . H69 H 0.8439 0.4756 0.4523 0.0630 1.0000 Uiso R . . . . . . H70 H 0.7961 0.6021 0.4858 0.0628 1.0000 Uiso R . . . . . . H71 H 1.0514 0.4614 0.3888 0.0591 1.0000 Uiso R . . . . . . C72 C 1.5406(5) 0.2296(5) 0.6630(5) 0.0436 0.5188 Uani . . . . 2 . . C73 C 1.4741(5) 0.2908(6) 0.5648(4) 0.0364 0.4812 Uani . . . . 1 . . C74 C 1.6129(10) 0.3023(10) 0.5903(10) 0.0478 0.4812 Uani . . . . 1 . . C75 C 1.5779(11) 0.3473(10) 0.5891(8) 0.0507 0.5188 Uani . . . . 2 . . O76 O 1.6190(8) 0.4073(8) 0.6303(7) 0.0454 0.4812 Uani . . . . 1 . . O77 O 1.5865(8) 0.4515(7) 0.6306(8) 0.0529 0.5188 Uani . . . . 2 . . C78 C 1.5425(6) 0.3887(6) 0.7132(5) 0.0437 0.4812 Uani . . . . 1 . . C79 C 1.4647(6) 0.4785(6) 0.6728(5) 0.0467 0.5188 Uani . . . . 2 . . C80 C 1.4024(7) 0.3769(7) 0.6875(6) 0.0408 0.4812 Uani . . . . 1 . . C81 C 1.4240(7) 0.3600(6) 0.7436(6) 0.0446 0.5188 Uani . . . . 2 . . O82 O 1.4167(4) 0.2555(4) 0.7016(4) 0.0402 0.5188 Uani . . . . 2 . . O83 O 1.3936(4) 0.2721(4) 0.6467(4) 0.0348 0.4812 Uani . . . . 1 . . H84 H 1.3486 0.3614 0.7443 0.0507 0.4812 Uiso R . . . 1 . . H85 H 1.3373 0.3796 0.7684 0.0565 0.5188 Uiso R . . . 2 . . H86 H 1.4872 0.3322 0.7968 0.0560 0.5188 Uiso R . . . 2 . . H87 H 1.3683 0.4572 0.6415 0.0500 0.4812 Uiso R . . . 1 . . H88 H 1.3974 0.5121 0.6221 0.0570 0.5188 Uiso R . . . 2 . . H89 H 1.5470 0.4626 0.7395 0.0531 0.4812 Uiso R . . . 1 . . H90 H 1.4770 0.5450 0.7057 0.0570 0.5188 Uiso R . . . 2 . . H91 H 1.5760 0.3097 0.7603 0.0529 0.4812 Uiso R . . . 1 . . H92 H 1.6652 0.3270 0.5675 0.0587 0.5188 Uiso R . . . 2 . . H93 H 1.6643 0.3179 0.5315 0.0673 0.4812 Uiso R . . . 1 . . H94 H 1.5166 0.3728 0.5355 0.0582 0.5188 Uiso R . . . 2 . . H95 H 1.4410 0.3700 0.5171 0.0463 0.4812 Uiso R . . . 1 . . H96 H 1.6485 0.2223 0.6363 0.0671 0.4812 Uiso R . . . 1 . . H97 H 1.4706 0.2180 0.5390 0.0458 0.4812 Uiso R . . . 1 . . H98 H 1.6057 0.2051 0.7145 0.0519 0.5188 Uiso R . . . 2 . . H99 H 1.5347 0.1592 0.6333 0.0521 0.5188 Uiso R . . . 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 O1 0.0411(10) 0.0384(11) 0.0271(9) -0.0084(8) -0.0027(8) -0.0006(8) N2 0.0329(11) 0.0231(10) 0.0296(11) -0.0063(8) 0.0030(9) -0.0026(8) O3 0.0293(10) 0.0413(11) 0.0400(10) -0.0144(9) 0.0100(8) -0.0079(8) N4 0.0246(10) 0.0292(11) 0.0292(10) -0.0112(9) 0.0008(8) -0.0005(8) C5 0.0226(12) 0.0464(15) 0.0306(13) -0.0197(12) 0.0023(10) -0.0032(10) N6 0.0238(11) 0.0788(19) 0.0513(15) -0.0472(14) 0.0023(10) -0.0051(11) N7 0.0388(14) 0.080(2) 0.0703(19) -0.0596(17) -0.0052(13) 0.0036(13) O8 0.0377(12) 0.0679(15) 0.0689(15) -0.0431(13) -0.0010(10) -0.0063(10) O9 0.0409(13) 0.116(2) 0.143(3) -0.110(2) -0.0049(15) 0.0094(14) C10 0.0224(12) 0.070(2) 0.0451(16) -0.0382(15) -0.0009(11) 0.0007(12) C11 0.0232(11) 0.0309(13) 0.0318(13) -0.0133(10) -0.0012(9) 0.0020(9) N12 0.0239(10) 0.0314(11) 0.0231(10) -0.0080(8) -0.0006(8) -0.0011(8) N13 0.0228(10) 0.0364(12) 0.0269(10) -0.0134(9) 0.0028(8) -0.0034(8) O14 0.0387(11) 0.0328(10) 0.0553(12) -0.0194(9) -0.0008(9) -0.0092(8) O15 0.0402(11) 0.0413(11) 0.0312(10) -0.0078(8) -0.0123(8) 0.0001(8) C16 0.0223(12) 0.0378(14) 0.0280(12) 0.0014(11) 0.0028(9) -0.0028(10) N17 0.0210(10) 0.0302(11) 0.0322(11) 0.0000(9) 0.0018(8) -0.0001(8) C18 0.0214(12) 0.0513(16) 0.0242(12) -0.0044(11) 0.0015(9) -0.0027(11) N19 0.0225(12) 0.113(3) 0.0216(11) 0.0053(13) -0.0012(9) -0.0050(13) C20 0.0226(13) 0.085(2) 0.0230(13) 0.0000(14) 0.0017(10) -0.0034(13) N21 0.0224(11) 0.092(2) 0.0270(11) -0.0250(13) 0.0056(9) -0.0032(12) N22 0.0213(13) 0.201(5) 0.0318(16) -0.047(2) -0.0046(11) 0.022(2) O23 0.0347(14) 0.229(4) 0.075(2) -0.107(3) -0.0060(12) 0.026(2) O24 0.0514(17) 0.253(5) 0.0258(13) 0.006(2) 0.0125(12) 0.058(2) N26 0.0336(12) 0.0457(13) 0.0243(11) -0.0103(10) -0.0030(9) 0.0022(10) O27 0.0447(12) 0.0721(15) 0.0224(9) -0.0081(9) 0.0045(8) -0.0017(10) O28 0.0340(12) 0.107(2) 0.0385(12) -0.0094(12) -0.0119(9) -0.0109(12) N30 0.0311(12) 0.0345(12) 0.0325(12) 0.0039(10) 0.0023(9) 0.0019(9) O31 0.0244(10) 0.0524(13) 0.0484(12) -0.0031(10) -0.0005(8) 0.0068(8) O32 0.0391(11) 0.0346(11) 0.0538(13) -0.0059(9) 0.0008(9) -0.0013(9) O37 0.0311(11) 0.0804(17) 0.0488(13) -0.0147(12) 0.0044(9) 0.0011(10) C38 0.0283(14) 0.096(3) 0.0322(15) -0.0085(16) 0.0046(12) 0.0047(15) C39 0.0273(14) 0.108(3) 0.0325(15) -0.0231(17) 0.0035(12) -0.0061(16) O40 0.0249(10) 0.120(2) 0.0345(11) -0.0260(12) 0.0064(8) -0.0161(11) C41 0.0262(14) 0.118(3) 0.0309(15) -0.0221(18) 0.0059(12) -0.0117(17) C42 0.0347(17) 0.108(3) 0.0485(19) -0.030(2) 0.0021(14) 0.0070(18) O51 0.0355(11) 0.0269(10) 0.117(2) -0.0179(12) 0.0213(13) -0.0048(8) C52 0.0404(17) 0.0277(15) 0.112(3) -0.0188(17) 0.0196(18) 0.0004(12) C53 0.0447(18) 0.0309(16) 0.108(3) -0.0188(18) 0.0121(19) -0.0045(13) O54 0.0398(12) 0.0280(11) 0.101(2) -0.0091(12) 0.0174(12) -0.0058(9) C55 0.0402(17) 0.0328(16) 0.107(3) -0.0168(18) 0.0155(18) 0.0022(13) C56 0.0398(18) 0.0399(18) 0.119(4) -0.028(2) 0.010(2) -0.0051(14) C66 0.062(2) 0.0401(17) 0.0463(17) -0.0133(14) 0.0000(15) -0.0005(14) O67 0.0616(14) 0.0367(11) 0.0468(12) -0.0017(9) -0.0028(10) 0.0065(10) C68 0.0555(19) 0.0445(18) 0.0518(19) -0.0037(15) -0.0058(15) 0.0058(15) C72 0.032(3) 0.033(3) 0.064(4) -0.009(3) 0.002(3) -0.007(2) C73 0.038(3) 0.033(3) 0.041(3) -0.012(2) 0.008(2) -0.008(2) C74 0.031(5) 0.041(6) 0.069(6) -0.013(5) 0.002(4) -0.002(4) C75 0.044(6) 0.042(6) 0.056(5) 0.002(5) 0.020(4) -0.007(4) O76 0.038(4) 0.043(5) 0.055(3) -0.009(4) 0.001(3) -0.017(3) O77 0.043(4) 0.032(4) 0.081(4) -0.008(4) 0.019(3) -0.014(3) C78 0.051(4) 0.037(3) 0.044(3) -0.009(3) -0.006(3) -0.013(3) C79 0.041(3) 0.036(3) 0.064(4) -0.013(3) 0.009(3) -0.009(2) C80 0.044(4) 0.041(4) 0.040(4) -0.014(3) 0.008(3) -0.009(3) C81 0.047(4) 0.034(3) 0.055(4) -0.012(3) 0.007(3) -0.014(3) O82 0.035(2) 0.033(2) 0.053(3) -0.011(2) 0.010(2) -0.0137(17) O83 0.036(2) 0.035(2) 0.035(2) -0.010(2) 0.007(2) -0.0116(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.17619(12) 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 . N2 . 1.222(3) yes N2 . O3 . 1.216(3) yes N2 . N4 . 1.377(3) yes N4 . C5 . 1.458(3) yes N4 . C11 . 1.467(3) yes C5 . N6 . 1.456(3) yes C5 . C18 . 1.572(4) yes C5 . H36 . 0.967 no N6 . N7 . 1.423(4) yes N6 . C10 . 1.488(3) yes N7 . O8 . 1.207(3) yes N7 . O9 . 1.215(3) yes C10 . C11 . 1.568(3) yes C10 . N21 . 1.437(4) yes C10 . H35 . 0.978 no C11 . N12 . 1.442(3) yes C11 . H34 . 0.972 no N12 . N13 . 1.404(3) yes N12 . C16 . 1.435(3) yes N13 . O14 . 1.211(3) yes N13 . O15 . 1.207(3) yes C16 . N17 . 1.478(3) yes C16 . C20 . 1.570(4) yes C16 . H33 . 0.966 no N17 . C18 . 1.458(3) yes N17 . N30 . 1.427(3) yes C18 . N19 . 1.450(3) yes C18 . H29 . 0.975 no N19 . C20 . 1.457(4) yes N19 . N26 . 1.343(3) yes C20 . N21 . 1.449(4) yes C20 . H25 . 0.981 no N21 . N22 . 1.415(4) yes N22 . O23 . 1.214(6) yes N22 . O24 . 1.217(6) yes N26 . O27 . 1.216(3) yes N26 . O28 . 1.217(3) yes N30 . O31 . 1.214(3) yes N30 . O32 . 1.207(3) yes O37 . C38 . 1.426(4) yes O37 . C42 . 1.434(4) yes C38 . C39 . 1.493(5) yes C38 . H49 . 0.976 no C38 . H50 . 0.964 no C39 . O40 . 1.433(3) yes C39 . H47 . 0.971 no C39 . H48 . 0.969 no O40 . C41 . 1.421(4) yes C41 . C42 . 1.499(6) yes C41 . H45 . 0.976 no C41 . H46 . 0.973 no C42 . H43 . 0.975 no C42 . H44 . 0.968 no O51 . C52 . 1.423(4) yes O51 . C56 . 1.415(5) yes C52 . C53 . 1.505(4) yes C52 . H63 . 0.968 no C52 . H64 . 0.977 no C53 . O54 . 1.427(5) yes C53 . H61 . 0.975 no C53 . H62 . 0.976 no O54 . C55 . 1.428(4) yes C55 . C56 . 1.512(4) yes C55 . H59 . 0.980 no C55 . H60 . 0.971 no C56 . H57 . 0.980 no C56 . H58 . 0.965 no H65 . C66 . 0.978 no C66 . C68 2_766 1.499(4) yes C66 . O67 . 1.420(4) yes C66 . H71 . 0.968 no O67 . C68 . 1.430(4) yes C68 . H69 . 0.984 no C68 . H70 . 0.978 no C72 . C75 . 1.494(11) yes C72 . O82 . 1.427(7) yes C72 . H98 . 0.975 no C72 . H99 . 0.977 no C73 . C74 . 1.505(12) yes C73 . O83 . 1.422(7) yes C73 . H95 . 0.975 no C73 . H97 . 0.962 no C74 . O76 . 1.413(14) yes C74 . H93 . 0.984 no C74 . H96 . 0.977 no C75 . O77 . 1.422(14) yes C75 . H92 . 0.977 no C75 . H94 . 0.970 no O76 . C78 . 1.410(12) yes O77 . C79 . 1.436(10) yes C78 . C80 . 1.519(9) yes C78 . H89 . 0.978 no C78 . H91 . 0.970 no C79 . C81 . 1.489(9) yes C79 . H88 . 0.986 no C79 . H90 . 0.981 no C80 . O83 . 1.423(8) yes C80 . H84 . 0.974 no C80 . H87 . 0.974 no C81 . O82 . 1.428(8) yes C81 . H85 . 0.988 no C81 . H86 . 0.979 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 O1 . N2 . O3 . 127.3(2) yes O1 . N2 . N4 . 116.1(2) yes O3 . N2 . N4 . 116.5(2) yes N2 . N4 . C5 . 119.52(19) yes N2 . N4 . C11 . 121.30(19) yes C5 . N4 . C11 . 110.94(19) yes N4 . C5 . N6 . 99.21(19) yes N4 . C5 . C18 . 113.2(2) yes N6 . C5 . C18 . 109.8(2) yes N4 . C5 . H36 . 112.1 no N6 . C5 . H36 . 111.0 no C18 . C5 . H36 . 111.0 no C5 . N6 . N7 . 114.5(2) yes C5 . N6 . C10 . 107.33(19) yes N7 . N6 . C10 . 115.4(2) yes N6 . N7 . O8 . 116.3(2) yes N6 . N7 . O9 . 116.5(3) yes O8 . N7 . O9 . 127.0(3) yes N6 . C10 . C11 . 105.7(2) yes N6 . C10 . N21 . 110.9(2) yes C11 . C10 . N21 . 108.3(2) yes N6 . C10 . H35 . 110.5 no C11 . C10 . H35 . 110.6 no N21 . C10 . H35 . 110.7 no C10 . C11 . N4 . 99.69(18) yes C10 . C11 . N12 . 108.5(2) yes N4 . C11 . N12 . 114.75(19) yes C10 . C11 . H34 . 111.1 no N4 . C11 . H34 . 112.2 no N12 . C11 . H34 . 110.1 no C11 . N12 . N13 . 119.58(19) yes C11 . N12 . C16 . 117.0(2) yes N13 . N12 . C16 . 119.4(2) yes N12 . N13 . O14 . 116.4(2) yes N12 . N13 . O15 . 116.8(2) yes O14 . N13 . O15 . 126.7(2) yes N12 . C16 . N17 . 109.85(19) yes N12 . C16 . C20 . 108.5(2) yes N17 . C16 . C20 . 105.1(2) yes N12 . C16 . H33 . 110.4 no N17 . C16 . H33 . 109.8 no C20 . C16 . H33 . 113.1 no C16 . N17 . C18 . 107.5(2) yes C16 . N17 . N30 . 115.4(2) yes C18 . N17 . N30 . 116.2(2) yes C5 . C18 . N17 . 108.32(19) yes C5 . C18 . N19 . 109.5(2) yes N17 . C18 . N19 . 102.9(2) yes C5 . C18 . H29 . 111.1 no N17 . C18 . H29 . 111.9 no N19 . C18 . H29 . 112.8 no C18 . N19 . C20 . 109.8(2) yes C18 . N19 . N26 . 123.6(2) yes C20 . N19 . N26 . 123.2(2) yes C16 . C20 . N19 . 102.7(2) yes C16 . C20 . N21 . 108.2(2) yes N19 . C20 . N21 . 112.3(3) yes C16 . C20 . H25 . 111.1 no N19 . C20 . H25 . 110.7 no N21 . C20 . H25 . 111.6 no C20 . N21 . C10 . 116.0(2) yes C20 . N21 . N22 . 116.4(3) yes C10 . N21 . N22 . 115.3(3) yes N21 . N22 . O23 . 117.5(4) yes N21 . N22 . O24 . 114.7(5) yes O23 . N22 . O24 . 127.6(3) yes N19 . N26 . O27 . 116.6(2) yes N19 . N26 . O28 . 116.2(2) yes O27 . N26 . O28 . 127.2(2) yes N17 . N30 . O31 . 116.0(2) yes N17 . N30 . O32 . 116.3(2) yes O31 . N30 . O32 . 127.6(2) yes C38 . O37 . C42 . 108.8(2) yes O37 . C38 . C39 . 110.3(3) yes O37 . C38 . H49 . 110.4 no C39 . C38 . H49 . 108.2 no O37 . C38 . H50 . 109.1 no C39 . C38 . H50 . 108.0 no H49 . C38 . H50 . 110.7 no C38 . C39 . O40 . 110.3(3) yes C38 . C39 . H47 . 109.7 no O40 . C39 . H47 . 108.1 no C38 . C39 . H48 . 110.4 no O40 . C39 . H48 . 108.3 no H47 . C39 . H48 . 109.9 no C39 . O40 . C41 . 109.6(2) yes O40 . C41 . C42 . 111.5(3) yes O40 . C41 . H45 . 109.3 no C42 . C41 . H45 . 110.3 no O40 . C41 . H46 . 108.3 no C42 . C41 . H46 . 108.7 no H45 . C41 . H46 . 108.6 no C41 . C42 . O37 . 110.7(3) yes C41 . C42 . H43 . 110.7 no O37 . C42 . H43 . 108.3 no C41 . C42 . H44 . 109.3 no O37 . C42 . H44 . 108.5 no H43 . C42 . H44 . 109.3 no C52 . O51 . C56 . 109.8(3) yes O51 . C52 . C53 . 110.7(3) yes O51 . C52 . H63 . 108.3 no C53 . C52 . H63 . 109.4 no O51 . C52 . H64 . 108.5 no C53 . C52 . H64 . 110.8 no H63 . C52 . H64 . 109.1 no C52 . C53 . O54 . 111.1(3) yes C52 . C53 . H61 . 109.7 no O54 . C53 . H61 . 108.7 no C52 . C53 . H62 . 109.6 no O54 . C53 . H62 . 108.9 no H61 . C53 . H62 . 108.8 no C53 . O54 . C55 . 109.9(3) yes O54 . C55 . C56 . 110.5(3) yes O54 . C55 . H59 . 107.5 no C56 . C55 . H59 . 109.6 no O54 . C55 . H60 . 108.9 no C56 . C55 . H60 . 111.4 no H59 . C55 . H60 . 108.9 no C55 . C56 . O51 . 111.8(3) yes C55 . C56 . H57 . 108.6 no O51 . C56 . H57 . 108.3 no C55 . C56 . H58 . 109.0 no O51 . C56 . H58 . 109.0 no H57 . C56 . H58 . 110.1 no C68 2_766 C66 . H65 . 110.0 no C68 2_766 C66 . O67 . 110.6(3) yes H65 . C66 . O67 . 108.1 no C68 2_766 C66 . H71 . 109.8 no H65 . C66 . H71 . 108.9 no O67 . C66 . H71 . 109.4 no C66 . O67 . C68 . 108.3(2) yes C66 2_766 C68 . O67 . 111.3(3) yes C66 2_766 C68 . H69 . 108.8 no O67 . C68 . H69 . 108.9 no C66 2_766 C68 . H70 . 109.4 no O67 . C68 . H70 . 108.4 no H69 . C68 . H70 . 110.0 no C75 . C72 . O82 . 110.4(5) yes C75 . C72 . H98 . 109.1 no O82 . C72 . H98 . 109.0 no C75 . C72 . H99 . 109.2 no O82 . C72 . H99 . 108.5 no H98 . C72 . H99 . 110.6 no C74 . C73 . O83 . 111.2(7) yes C74 . C73 . H95 . 109.2 no O83 . C73 . H95 . 108.9 no C74 . C73 . H97 . 109.5 no O83 . C73 . H97 . 108.6 no H95 . C73 . H97 . 109.4 no C73 . C74 . O76 . 110.0(7) yes C73 . C74 . H93 . 108.4 no O76 . C74 . H93 . 109.3 no C73 . C74 . H96 . 110.1 no O76 . C74 . H96 . 109.4 no H93 . C74 . H96 . 109.5 no C72 . C75 . O77 . 110.2(9) yes C72 . C75 . H92 . 107.7 no O77 . C75 . H92 . 106.7 no C72 . C75 . H94 . 111.4 no O77 . C75 . H94 . 110.3 no H92 . C75 . H94 . 110.5 no C74 . O76 . C78 . 110.2(9) yes C75 . O77 . C79 . 110.1(8) yes O76 . C78 . C80 . 109.5(6) yes O76 . C78 . H89 . 109.1 no C80 . C78 . H89 . 110.1 no O76 . C78 . H91 . 109.3 no C80 . C78 . H91 . 109.4 no H89 . C78 . H91 . 109.5 no O77 . C79 . C81 . 111.0(6) yes O77 . C79 . H88 . 109.5 no C81 . C79 . H88 . 110.1 no O77 . C79 . H90 . 107.5 no C81 . C79 . H90 . 109.2 no H88 . C79 . H90 . 109.4 no C78 . C80 . O83 . 111.2(5) yes C78 . C80 . H84 . 110.7 no O83 . C80 . H84 . 107.8 no C78 . C80 . H87 . 109.2 no O83 . C80 . H87 . 109.0 no H84 . C80 . H87 . 108.9 no C79 . C81 . O82 . 111.7(6) yes C79 . C81 . H85 . 109.4 no O82 . C81 . H85 . 108.5 no C79 . C81 . H86 . 109.5 no O82 . C81 . H86 . 108.3 no H85 . C81 . H86 . 109.3 no C81 . O82 . C72 . 108.7(4) yes C80 . O83 . C73 . 108.9(5) 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 C20 . H25 . O83 . 126 0.98 2.29 2.976(7) yes C18 . H29 . O40 . 132 0.97 2.28 3.025(7) yes C11 . H34 . O54 2_747 147 0.97 2.19 3.048(7) yes C10 . H35 . O37 1_655 128 0.98 2.53 3.228(7) yes C5 . H36 . O40 . 127 0.97 2.40 3.083(7) yes C38 . H49 . O51 . 166 0.98 2.51 3.467(7) yes C38 . H50 . O15 1_455 142 0.96 2.54 3.352(7) yes C52 . H64 . O8 . 139 0.98 2.56 3.354(7) yes C66 . H65 . O76 2_866 143 0.98 2.48 3.312(7) yes C66 . H71 . O8 2_756 163 0.97 2.52 3.455(7) yes C73 . H95 . O77 2_866 162 0.97 2.45 3.393(7) yes C73 . H97 . O24 . 146 0.96 2.27 3.114(7) yes # Attachment '- cl20gbl.cif' data_cl20gbl _database_code_depnum_ccdc_archive 'CCDC 832146' #TrackingRef '- cl20gbl.cif' _audit_creation_date 11-06-23 _audit_creation_method CRYSTALS_ver_12.87 _oxford_structure_analysis_title 'CL-20:g-butyrolactone (1:1) Co-crystal' _chemical_name_systematic 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane: _chemical_melting_point ? _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 15.7503(9) _cell_length_b 20.5096(13) _cell_length_c 23.2073(13) _cell_angle_alpha 90 _cell_angle_beta 90.092(2) _cell_angle_gamma 90 _cell_volume 7496.7(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 c 1 ' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z x,-y,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 12 # Given Formula = C10 H12 N12 O14 # Dc = 1.39 Fooo = 4284.00 Mu = 1.30 M = 1572.83 # Found Formula = C13.33 H15.67 N16 O18.67 # Dc = 1.86 FOOO = 4284.00 Mu = 1.73 M = 2096.10 _chemical_formula_sum 'C13.33 H15.67 N16 O18.67' _chemical_formula_moiety 'C13.33 H15.67 N16 O18.67' _chemical_compound_source ? _chemical_formula_weight 698.70 _cell_measurement_reflns_used 6564 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _cell_measurement_temperature 100 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_min 0.050 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_max 0.290 _exptl_crystal_density_diffrn 1.857 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 4284 _exptl_absorpt_coefficient_mu 0.173 # 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 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 6564 _reflns_number_total 6564 _diffrn_reflns_av_R_equivalents 0.048 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 6564 # Theoretical number of reflections is about 13243 _diffrn_reflns_theta_min 1.630 _diffrn_reflns_theta_max 25.026 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.026 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -18 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 24 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.49 _refine_diff_density_max 0.92 # 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>-10.0\s(I) _refine_ls_number_reflns 6542 _refine_ls_number_restraints 2 _refine_ls_number_parameters 582 _oxford_refine_ls_R_factor_ref 0.0627 _refine_ls_wR_factor_ref 0.1336 _refine_ls_goodness_of_fit_ref 0.9669 _refine_ls_shift/su_max 0.0137647 _refine_ls_shift/su_mean 0.0915928 # The values computed from all data _oxford_reflns_number_all 6542 _refine_ls_R_factor_all 0.0627 _refine_ls_wR_factor_all 0.1336 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5629 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_gt 0.1264 # 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 unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # 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^) + ( 0.06P)^2^ +48.07P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 N14 N -0.0739(5) 0.6519(4) 0.2196(3) 0.0178(16) 1.0000 Uiso . . . . . . . N16 N -0.0383(4) 0.6276(3) 0.2718(3) 0.0130(15) 1.0000 Uiso . . . . . . . N18 N -0.0386(4) 0.6963(3) 0.3517(3) 0.0138(14) 1.0000 Uiso . . . . . . . N19 N -0.0701(5) 0.7600(4) 0.3464(3) 0.0244(17) 1.0000 Uiso . . . . . . . N24 N -0.0669(4) 0.5350(3) 0.3317(3) 0.0120(14) 1.0000 Uiso . . . . . . . N25 N -0.0846(5) 0.4807(4) 0.2960(3) 0.0176(16) 1.0000 Uiso . . . . . . . N29 N 0.0826(4) 0.5615(3) 0.3200(3) 0.0117(14) 1.0000 Uiso . . . . . . . N31 N 0.0800(4) 0.6256(3) 0.3980(3) 0.0111(14) 1.0000 Uiso . . . . . . . N33 N -0.0717(4) 0.6080(3) 0.4160(3) 0.0106(14) 1.0000 Uiso . . . . . . . N34 N -0.1062(4) 0.6225(3) 0.4697(3) 0.0144(15) 1.0000 Uiso . . . . . . . N37 N 0.0930(4) 0.6805(3) 0.4319(3) 0.0149(14) 1.0000 Uiso . . . . . . . N40 N 0.1608(4) 0.5273(3) 0.3252(3) 0.0140(14) 1.0000 Uiso . . . . . . . N44 N 0.4395(4) 0.6639(3) 0.2264(3) 0.0142(15) 1.0000 Uiso . . . . . . . N47 N 0.4338(4) 0.5412(3) 0.3344(3) 0.0118(14) 1.0000 Uiso . . . . . . . N48 N 0.4373(5) 0.4887(4) 0.2959(3) 0.0191(16) 1.0000 Uiso . . . . . . . N52 N 0.5779(4) 0.5811(3) 0.3451(3) 0.0139(14) 1.0000 Uiso . . . . . . . N53 N 0.6588(4) 0.5523(3) 0.3540(3) 0.0143(14) 1.0000 Uiso . . . . . . . N58 N 0.4270(4) 0.7032(3) 0.3524(3) 0.0118(14) 1.0000 Uiso . . . . . . . N60 N 0.3935(4) 0.6125(3) 0.4163(3) 0.0081(13) 1.0000 Uiso . . . . . . . N62 N 0.5376(4) 0.6497(3) 0.4196(3) 0.0123(14) 1.0000 Uiso . . . . . . . N63 N 0.5934(5) 0.6645(3) 0.4659(3) 0.0179(15) 1.0000 Uiso . . . . . . . N66 N 0.3416(4) 0.6209(3) 0.4645(3) 0.0148(15) 1.0000 Uiso . . . . . . . N69 N 0.4289(4) 0.7539(4) 0.3908(3) 0.0165(15) 1.0000 Uiso . . . . . . . N74 N 0.3470(4) 0.9158(3) 0.4358(3) 0.0163(15) 1.0000 Uiso . . . . . . . N76 N 0.2897(4) 0.9008(3) 0.4801(3) 0.0126(14) 1.0000 Uiso . . . . . . . N78 N 0.1447(4) 0.8669(3) 0.4793(3) 0.0101(13) 1.0000 Uiso . . . . . . . N79 N 0.0938(4) 0.8745(3) 0.4310(3) 0.0139(14) 1.0000 Uiso . . . . . . . N83 N 0.1775(4) 0.9550(3) 0.5464(3) 0.0148(15) 1.0000 Uiso . . . . . . . N84 N 0.1829(4) 1.0056(4) 0.5079(3) 0.0180(15) 1.0000 Uiso . . . . . . . N89 N 0.3261(4) 0.8301(3) 0.5542(3) 0.0153(15) 1.0000 Uiso . . . . . . . N91 N 0.1808(4) 0.7927(3) 0.5605(3) 0.0117(14) 1.0000 Uiso . . . . . . . N93 N 0.2139(4) 0.8879(3) 0.6180(3) 0.0105(14) 1.0000 Uiso . . . . . . . N94 N 0.1833(4) 0.9145(3) 0.6704(3) 0.0162(15) 1.0000 Uiso . . . . . . . N97 N 0.1764(4) 0.7372(3) 0.5970(3) 0.0153(15) 1.0000 Uiso . . . . . . . N100 N 0.4049(4) 0.8000(3) 0.5457(3) 0.0153(15) 1.0000 Uiso . . . . . . . N104 N 0.1657(4) 0.7699(3) 0.1051(3) 0.0142(15) 1.0000 Uiso . . . . . . . N106 N 0.1833(4) 0.7173(3) 0.0675(3) 0.0108(14) 1.0000 Uiso . . . . . . . N108 N 0.2134(4) 0.6220(3) 0.1248(3) 0.0115(14) 1.0000 Uiso . . . . . . . N109 N 0.1823(4) 0.5987(3) 0.1776(3) 0.0159(15) 1.0000 Uiso . . . . . . . N113 N 0.2100(4) 0.5558(3) 0.0446(3) 0.0129(14) 1.0000 Uiso . . . . . . . N115 N 0.1752(4) 0.6455(3) -0.0174(3) 0.0111(14) 1.0000 Uiso . . . . . . . N116 N 0.1410(4) 0.6320(3) -0.0720(3) 0.0133(14) 1.0000 Uiso . . . . . . . N121 N 0.3315(4) 0.6883(3) 0.0776(3) 0.0111(14) 1.0000 Uiso . . . . . . . N123 N 0.3276(4) 0.6272(3) -0.0019(3) 0.0123(14) 1.0000 Uiso . . . . . . . N124 N 0.3390(4) 0.5739(3) -0.0375(3) 0.0162(15) 1.0000 Uiso . . . . . . . N127 N 0.4105(4) 0.7226(3) 0.0727(3) 0.0150(15) 1.0000 Uiso . . . . . . . N130 N 0.1757(4) 0.4918(3) 0.0501(3) 0.0184(15) 1.0000 Uiso . . . . . . . O1 O 0.4027(4) 0.5250(3) 0.6195(2) 0.0139(12) 1.0000 Uiso . . . . . . . O6 O 0.5133(4) 0.4564(3) 0.6155(3) 0.0233(14) 1.0000 Uiso . . . . . . . O7 O 0.2700(4) 0.7043(3) 0.2765(3) 0.0204(13) 1.0000 Uiso . . . . . . . O9 O 0.1592(4) 0.7708(3) 0.2735(2) 0.0176(13) 1.0000 Uiso . . . . . . . O13 O -0.0423(4) 0.7009(3) 0.2000(3) 0.0266(15) 1.0000 Uiso . . . . . . . O15 O -0.1293(5) 0.6182(4) 0.1989(3) 0.0346(17) 1.0000 Uiso . . . . . . . O20 O -0.0360(4) 0.7957(3) 0.3119(3) 0.0281(15) 1.0000 Uiso . . . . . . . O21 O -0.1257(5) 0.7745(4) 0.3803(3) 0.0415(19) 1.0000 Uiso . . . . . . . O26 O -0.1468(4) 0.4873(3) 0.2647(3) 0.0273(15) 1.0000 Uiso . . . . . . . O27 O -0.0389(4) 0.4333(3) 0.2998(3) 0.0246(15) 1.0000 Uiso . . . . . . . O35 O -0.0782(4) 0.5920(3) 0.5099(3) 0.0212(13) 1.0000 Uiso . . . . . . . O36 O -0.1637(4) 0.6618(3) 0.4702(3) 0.0261(14) 1.0000 Uiso . . . . . . . O38 O 0.1362(4) 0.7234(3) 0.4101(2) 0.0185(13) 1.0000 Uiso . . . . . . . O39 O 0.0642(4) 0.6785(3) 0.4802(3) 0.0224(14) 1.0000 Uiso . . . . . . . O41 O 0.2253(4) 0.5590(3) 0.3283(3) 0.0207(13) 1.0000 Uiso . . . . . . . O42 O 0.1557(4) 0.4681(3) 0.3226(3) 0.0256(14) 1.0000 Uiso . . . . . . . O43 O 0.3942(4) 0.6301(3) 0.1979(3) 0.0224(14) 1.0000 Uiso . . . . . . . N45 N 0.4662(4) 0.6381(3) 0.2795(3) 0.0142(15) 1.0000 Uiso . . . . . . . O49 O 0.3887(4) 0.4919(3) 0.2555(3) 0.0322(16) 1.0000 Uiso . . . . . . . O50 O 0.4871(4) 0.4451(3) 0.3063(3) 0.0302(16) 1.0000 Uiso . . . . . . . O54 O 0.7189(4) 0.5889(3) 0.3593(3) 0.0254(14) 1.0000 Uiso . . . . . . . O55 O 0.6616(4) 0.4935(3) 0.3525(3) 0.0255(14) 1.0000 Uiso . . . . . . . O64 O 0.6548(4) 0.6976(3) 0.4535(3) 0.0215(13) 1.0000 Uiso . . . . . . . O65 O 0.5736(4) 0.6446(3) 0.5125(3) 0.0224(14) 1.0000 Uiso . . . . . . . O67 O 0.3720(4) 0.6068(3) 0.5109(3) 0.0189(13) 1.0000 Uiso . . . . . . . O68 O 0.2684(4) 0.6376(3) 0.4549(3) 0.0239(14) 1.0000 Uiso . . . . . . . O70 O 0.3687(4) 0.7579(3) 0.4240(3) 0.0230(14) 1.0000 Uiso . . . . . . . O71 O 0.4903(4) 0.7908(3) 0.3881(3) 0.0262(14) 1.0000 Uiso . . . . . . . O72 O 0.4683(4) 0.7175(3) 0.2127(3) 0.0250(15) 1.0000 Uiso . . . . . . . O73 O 0.3278(4) 0.8976(3) 0.3876(3) 0.0246(14) 1.0000 Uiso . . . . . . . O75 O 0.4071(4) 0.9496(3) 0.4484(3) 0.0229(14) 1.0000 Uiso . . . . . . . O80 O 0.1242(4) 0.8598(3) 0.3854(2) 0.0179(13) 1.0000 Uiso . . . . . . . O81 O 0.0212(4) 0.8934(3) 0.4403(3) 0.0226(14) 1.0000 Uiso . . . . . . . O85 O 0.1242(4) 1.0115(3) 0.4738(3) 0.0218(13) 1.0000 Uiso . . . . . . . O86 O 0.2453(4) 1.0418(3) 0.5126(3) 0.0285(15) 1.0000 Uiso . . . . . . . O95 O 0.2117(4) 0.9678(3) 0.6848(3) 0.0262(15) 1.0000 Uiso . . . . . . . O96 O 0.1356(4) 0.8798(3) 0.6981(3) 0.0245(14) 1.0000 Uiso . . . . . . . O98 O 0.2228(4) 0.6922(3) 0.5842(3) 0.0240(14) 1.0000 Uiso . . . . . . . O99 O 0.1246(4) 0.7394(3) 0.6356(3) 0.0248(15) 1.0000 Uiso . . . . . . . O101 O 0.4054(4) 0.7405(3) 0.5462(3) 0.0247(14) 1.0000 Uiso . . . . . . . O102 O 0.4665(4) 0.8347(3) 0.5412(3) 0.0266(15) 1.0000 Uiso . . . . . . . O103 O 0.2128(4) 0.8164(3) 0.1029(3) 0.0245(14) 1.0000 Uiso . . . . . . . O105 O 0.1030(4) 0.7641(3) 0.1344(3) 0.0237(14) 1.0000 Uiso . . . . . . . O110 O 0.1291(4) 0.6330(3) 0.2005(3) 0.0213(14) 1.0000 Uiso . . . . . . . O111 O 0.2156(4) 0.5505(3) 0.1976(3) 0.0224(14) 1.0000 Uiso . . . . . . . O117 O 0.1679(4) 0.6633(3) -0.1122(2) 0.0184(13) 1.0000 Uiso . . . . . . . O118 O 0.0852(4) 0.5916(3) -0.0722(3) 0.0231(14) 1.0000 Uiso . . . . . . . O125 O 0.3810(4) 0.5288(3) -0.0168(3) 0.0208(13) 1.0000 Uiso . . . . . . . O126 O 0.3086(4) 0.5760(3) -0.0854(3) 0.0242(14) 1.0000 Uiso . . . . . . . O128 O 0.4753(4) 0.6904(3) 0.0694(3) 0.0210(13) 1.0000 Uiso . . . . . . . O129 O 0.4055(4) 0.7819(3) 0.0768(3) 0.0269(15) 1.0000 Uiso . . . . . . . O131 O 0.2116(4) 0.4557(3) 0.0834(3) 0.0241(14) 1.0000 Uiso . . . . . . . O132 O 0.1160(4) 0.4792(3) 0.0192(3) 0.0296(15) 1.0000 Uiso . . . . . . . O133 O 0.6642(4) 0.7614(3) 0.2762(2) 0.0170(13) 1.0000 Uiso . . . . . . . O137 O 0.7831(5) 0.7058(4) 0.2849(4) 0.046(2) 1.0000 Uiso . . . . . . . O138 O 0.0356(4) 0.5511(3) 0.1180(3) 0.0321(16) 1.0000 Uiso . . . . . . . O140 O -0.0808(4) 0.4890(3) 0.1169(3) 0.0210(14) 1.0000 Uiso . . . . . . . C1 C 0.0373(7) 0.4458(5) 0.1653(5) 0.031(2) 1.0000 Uiso . . . . . . . C2 C 0.3846(5) 0.5892(4) 0.6413(4) 0.0156(18) 1.0000 Uiso . . . . . . . C3 C 0.4699(5) 0.6240(4) 0.6450(4) 0.0194(19) 1.0000 Uiso . . . . . . . C4 C 0.5310(6) 0.5673(4) 0.6529(4) 0.0181(19) 1.0000 Uiso . . . . . . . C5 C 0.4856(5) 0.5097(4) 0.6274(3) 0.0129(17) 1.0000 Uiso . . . . . . . C8 C 0.2423(5) 0.7583(4) 0.2669(4) 0.0150(18) 1.0000 Uiso . . . . . . . C10 C 0.1405(5) 0.8374(4) 0.2557(4) 0.0125(17) 1.0000 Uiso . . . . . . . C11 C 0.2251(6) 0.8724(4) 0.2568(4) 0.0214(19) 1.0000 Uiso . . . . . . . C12 C 0.2883(6) 0.8180(4) 0.2455(4) 0.0190(19) 1.0000 Uiso . . . . . . . C13 C -0.0261(6) 0.3901(5) 0.1543(4) 0.028(2) 1.0000 Uiso . . . . . . . C17 C 0.0160(5) 0.6712(4) 0.3046(3) 0.0125(17) 1.0000 Uiso . . . . . . . C22 C -0.1014(5) 0.6441(4) 0.3655(3) 0.0141(17) 1.0000 Uiso . . . . . . . C23 C -0.0978(5) 0.5977(4) 0.3124(3) 0.0117(17) 1.0000 Uiso . . . . . . . C28 C 0.0162(5) 0.5335(4) 0.3588(3) 0.0092(16) 1.0000 Uiso . . . . . . . C30 C 0.0890(5) 0.6302(4) 0.3350(3) 0.0124(16) 1.0000 Uiso . . . . . . . C32 C 0.0126(5) 0.5798(4) 0.4124(3) 0.0103(15) 1.0000 Uiso . . . . . . . C46 C 0.4005(5) 0.6017(4) 0.3118(3) 0.0116(17) 1.0000 Uiso . . . . . . . C51 C 0.5070(5) 0.5475(4) 0.3729(3) 0.0113(16) 1.0000 Uiso . . . . . . . C56 C 0.5721(5) 0.6502(4) 0.3608(3) 0.0135(17) 1.0000 Uiso . . . . . . . C57 C 0.5037(5) 0.6849(4) 0.3205(3) 0.0129(17) 1.0000 Uiso . . . . . . . C59 C 0.3734(5) 0.6458(4) 0.3628(3) 0.0124(17) 1.0000 Uiso . . . . . . . C60 C 0.7797(10) 0.8284(8) 0.2641(7) 0.017(4) 0.5000 Uiso . . . . 1 . . C61 C 0.4808(5) 0.5932(4) 0.4246(3) 0.0123(16) 1.0000 Uiso . . . . . . . C142 C 0.7826(12) 0.8026(9) 0.2300(8) 0.022(4) 0.5000 Uiso . . . . 2 . . C77 C 0.2312(5) 0.8455(4) 0.4726(3) 0.0136(17) 1.0000 Uiso . . . . . . . C82 C 0.1240(5) 0.8988(4) 0.5328(3) 0.0083(16) 1.0000 Uiso . . . . . . . C87 C 0.2527(5) 0.9345(4) 0.5783(3) 0.0138(17) 1.0000 Uiso . . . . . . . C88 C 0.3211(5) 0.8992(4) 0.5393(3) 0.0124(16) 1.0000 Uiso . . . . . . . C90 C 0.2535(5) 0.7983(4) 0.5240(3) 0.0125(17) 1.0000 Uiso . . . . . . . C92 C 0.1468(5) 0.8529(4) 0.5843(3) 0.0105(17) 1.0000 Uiso . . . . . . . C107 C 0.1520(5) 0.6543(4) 0.0857(3) 0.0103(17) 1.0000 Uiso . . . . . . . C112 C 0.2655(5) 0.5797(4) 0.0900(3) 0.0124(17) 1.0000 Uiso . . . . . . . C114 C 0.1474(5) 0.6082(4) 0.0316(3) 0.0106(16) 1.0000 Uiso . . . . . . . C119 C 0.2600(5) 0.6737(4) -0.0151(3) 0.0077(15) 1.0000 Uiso . . . . . . . C120 C 0.2636(5) 0.7183(4) 0.0402(3) 0.0131(17) 1.0000 Uiso . . . . . . . C122 C 0.3392(5) 0.6210(4) 0.0602(3) 0.0146(17) 1.0000 Uiso . . . . . . . C134 C 0.6355(5) 0.8257(4) 0.2578(4) 0.0132(17) 1.0000 Uiso . . . . . . . C135 C 0.7151(7) 0.8605(5) 0.2358(5) 0.032(2) 1.0000 Uiso . . . . . . . C136 C 0.7486(7) 0.7551(6) 0.2701(5) 0.035(3) 1.0000 Uiso . . . . . . . C139 C 0.0004(6) 0.5002(5) 0.1307(4) 0.022(2) 1.0000 Uiso . . . . . . . C141 C -0.1076(6) 0.4253(4) 0.1383(4) 0.0187(19) 1.0000 Uiso . . . . . . . H12 H 0.0390 0.4559 0.2063 0.0425 1.0000 Uiso R . . . . . . H11 H 0.0948 0.4335 0.1524 0.0413 1.0000 Uiso R . . . . . . H21 H 0.3578 0.5874 0.6794 0.0186 1.0000 Uiso R . . . . . . H22 H 0.3468 0.6107 0.6138 0.0185 1.0000 Uiso R . . . . . . H32 H 0.4719 0.6532 0.6769 0.0264 1.0000 Uiso R . . . . . . H31 H 0.4818 0.6465 0.6094 0.0264 1.0000 Uiso R . . . . . . H42 H 0.5414 0.5610 0.6933 0.0252 1.0000 Uiso R . . . . . . H41 H 0.5844 0.5748 0.6335 0.0250 1.0000 Uiso R . . . . . . H101 H 0.1019 0.8566 0.2833 0.0159 1.0000 Uiso R . . . . . . H102 H 0.1155 0.8381 0.2169 0.0160 1.0000 Uiso R . . . . . . H112 H 0.2351 0.8935 0.2944 0.0270 1.0000 Uiso R . . . . . . H111 H 0.2274 0.9057 0.2267 0.0264 1.0000 Uiso R . . . . . . H122 H 0.3410 0.8237 0.2661 0.0231 1.0000 Uiso R . . . . . . H121 H 0.3003 0.8121 0.2048 0.0230 1.0000 Uiso R . . . . . . H131 H -0.0325 0.3634 0.1878 0.0405 1.0000 Uiso R . . . . . . H132 H -0.0057 0.3658 0.1216 0.0400 1.0000 Uiso R . . . . . . H171 H 0.0385 0.7069 0.2811 0.0159 1.0000 Uiso R . . . . . . H221 H -0.1583 0.6615 0.3713 0.0185 1.0000 Uiso R . . . . . . H231 H -0.1550 0.5941 0.2960 0.0168 1.0000 Uiso R . . . . . . H281 H 0.0313 0.4893 0.3702 0.0119 1.0000 Uiso R . . . . . . H301 H 0.1451 0.6469 0.3242 0.0124 1.0000 Uiso R . . . . . . H321 H 0.0263 0.5582 0.4486 0.0140 1.0000 Uiso R . . . . . . H461 H 0.3524 0.5924 0.2868 0.0140 1.0000 Uiso R . . . . . . H511 H 0.5237 0.5045 0.3870 0.0150 1.0000 Uiso R . . . . . . H561 H 0.6269 0.6728 0.3585 0.0180 1.0000 Uiso R . . . . . . H571 H 0.5291 0.7221 0.3005 0.0153 1.0000 Uiso R . . . . . . H591 H 0.3142 0.6565 0.3621 0.0140 1.0000 Uiso R . . . . . . H611 H 0.4889 0.5724 0.4624 0.0159 1.0000 Uiso R . . . . . . H771 H 0.2387 0.8229 0.4352 0.0156 1.0000 Uiso R . . . . . . H821 H 0.0634 0.9108 0.5327 0.0119 1.0000 Uiso R . . . . . . H871 H 0.2774 0.9713 0.5994 0.0176 1.0000 Uiso R . . . . . . H881 H 0.3766 0.9208 0.5424 0.0189 1.0000 Uiso R . . . . . . H901 H 0.2699 0.7552 0.5101 0.0149 1.0000 Uiso R . . . . . . H921 H 0.0975 0.8446 0.6089 0.0131 1.0000 Uiso R . . . . . . H1071 H 0.0964 0.6573 0.1044 0.0137 1.0000 Uiso R . . . . . . H1121 H 0.2877 0.5428 0.1120 0.0175 1.0000 Uiso R . . . . . . H1141 H 0.0903 0.5905 0.0255 0.0139 1.0000 Uiso R . . . . . . H1191 H 0.2728 0.6991 -0.0504 0.0117 1.0000 Uiso R . . . . . . H1201 H 0.2795 0.7627 0.0294 0.0149 1.0000 Uiso R . . . . . . H1221 H 0.3944 0.6019 0.0685 0.0148 1.0000 Uiso R . . . . . . H1342 H 0.6109 0.8494 0.2898 0.0182 1.0000 Uiso R . . . . . . H1341 H 0.5944 0.8205 0.2269 0.0187 1.0000 Uiso R . . . . . . H1412 H -0.1417 0.4303 0.1725 0.0255 1.0000 Uiso R . . . . . . H1411 H -0.1399 0.4034 0.1078 0.0255 1.0000 Uiso R . . . . . . H1422 H 0.8393 0.8165 0.2405 0.0238 0.5000 Uiso R . . . 2 . . H1421 H 0.7828 0.7849 0.1912 0.0240 0.5000 Uiso R . . . 2 . . H601 H 0.7890 0.8472 0.3010 0.0137 0.5000 Uiso R . . . 1 . . H602 H 0.8307 0.8304 0.2423 0.0137 0.5000 Uiso R . . . 1 . . H1351 H 0.7142 0.9054 0.2457 0.0382 0.5000 Uiso R . . . . . . H1352 H 0.7204 0.8561 0.1952 0.0382 0.5000 Uiso R . . . . . . _refine_ls_extinction_method None _oxford_refine_ls_scale 0.044559(7) loop_ _oxford_twin_element_scale_factors 0.776(2) 0.224(2) 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 N14 . N16 . 1.423(10) yes N14 . O13 . 1.210(10) yes N14 . O15 . 1.212(10) yes N16 . C17 . 1.452(10) yes N16 . C23 . 1.463(11) yes N18 . N19 . 1.404(10) yes N18 . C17 . 1.485(10) yes N18 . C22 . 1.493(11) yes N19 . O20 . 1.210(10) yes N19 . O21 . 1.215(10) yes N24 . N25 . 1.416(10) yes N24 . C23 . 1.445(10) yes N24 . C28 . 1.452(10) yes N25 . O26 . 1.225(10) yes N25 . O27 . 1.213(9) yes N29 . N40 . 1.422(9) yes N29 . C28 . 1.496(10) yes N29 . C30 . 1.455(10) yes N31 . N37 . 1.388(9) yes N31 . C30 . 1.471(10) yes N31 . C32 . 1.457(10) yes N33 . N34 . 1.394(9) yes N33 . C22 . 1.462(10) yes N33 . C32 . 1.450(10) yes N34 . O35 . 1.206(9) yes N34 . O36 . 1.212(9) yes N37 . O38 . 1.223(9) yes N37 . O39 . 1.212(9) yes N40 . O41 . 1.209(9) yes N40 . O42 . 1.217(9) yes N44 . O43 . 1.194(9) yes N44 . N45 . 1.404(10) yes N44 . O72 . 1.232(9) yes N47 . N48 . 1.400(10) yes N47 . C46 . 1.446(10) yes N47 . C51 . 1.463(10) yes N48 . O49 . 1.212(10) yes N48 . O50 . 1.214(10) yes N52 . N53 . 1.419(10) yes N52 . C51 . 1.463(10) yes N52 . C56 . 1.467(10) yes N53 . O54 . 1.213(9) yes N53 . O55 . 1.209(9) yes N58 . N69 . 1.369(10) yes N58 . C57 . 1.467(10) yes N58 . C59 . 1.470(10) yes N60 . N66 . 1.397(9) yes N60 . C59 . 1.451(10) yes N60 . C61 . 1.443(10) yes N62 . N63 . 1.419(9) yes N62 . C56 . 1.470(10) yes N62 . C61 . 1.469(10) yes N63 . O64 . 1.217(9) yes N63 . O65 . 1.198(9) yes N66 . O67 . 1.213(9) yes N66 . O68 . 1.223(9) yes N69 . O70 . 1.226(9) yes N69 . O71 . 1.230(9) yes N74 . N76 . 1.405(10) yes N74 . O73 . 1.216(9) yes N74 . O75 . 1.208(9) yes N76 . C77 . 1.472(10) yes N76 . C88 . 1.459(10) yes N78 . N79 . 1.385(9) yes N78 . C77 . 1.441(10) yes N78 . C82 . 1.440(10) yes N79 . O80 . 1.201(9) yes N79 . O81 . 1.227(9) yes N83 . N84 . 1.371(10) yes N83 . C82 . 1.463(10) yes N83 . C87 . 1.457(11) yes N84 . O85 . 1.223(9) yes N84 . O86 . 1.237(10) yes N89 . N100 . 1.400(10) yes N89 . C88 . 1.461(11) yes N89 . C90 . 1.491(10) yes N91 . N97 . 1.422(10) yes N91 . C90 . 1.429(10) yes N91 . C92 . 1.455(10) yes N93 . N94 . 1.419(10) yes N93 . C87 . 1.463(10) yes N93 . C92 . 1.497(10) yes N94 . O95 . 1.227(9) yes N94 . O96 . 1.218(9) yes N97 . O98 . 1.215(9) yes N97 . O99 . 1.213(9) yes N100 . O101 . 1.219(9) yes N100 . O102 . 1.209(9) yes N104 . N106 . 1.414(9) yes N104 . O103 . 1.209(9) yes N104 . O105 . 1.206(9) yes N106 . C107 . 1.446(10) yes N106 . C120 . 1.416(11) yes N108 . N109 . 1.404(10) yes N108 . C107 . 1.481(10) yes N108 . C112 . 1.442(10) yes N109 . O110 . 1.217(9) yes N109 . O111 . 1.212(9) yes N113 . N130 . 1.426(10) yes N113 . C112 . 1.452(10) yes N113 . C114 . 1.489(10) yes N115 . N116 . 1.405(9) yes N115 . C114 . 1.439(10) yes N115 . C119 . 1.457(10) yes N116 . O117 . 1.209(9) yes N116 . O118 . 1.208(9) yes N121 . N127 . 1.434(9) yes N121 . C120 . 1.507(10) yes N121 . C122 . 1.443(10) yes N123 . N124 . 1.381(9) yes N123 . C119 . 1.461(10) yes N123 . C122 . 1.459(10) yes N124 . O125 . 1.235(9) yes N124 . O126 . 1.211(9) yes N127 . O128 . 1.217(9) yes N127 . O129 . 1.223(9) yes N130 . O131 . 1.209(9) yes N130 . O132 . 1.210(9) yes O1 . C2 . 1.440(10) yes O1 . C5 . 1.356(10) yes O6 . C5 . 1.210(10) yes O7 . C8 . 1.211(10) yes O9 . C8 . 1.342(10) yes O9 . C10 . 1.457(10) yes N45 . C46 . 1.482(11) yes N45 . C57 . 1.473(10) yes O133 . C134 . 1.457(10) yes O133 . C136 . 1.344(12) yes O137 . C136 . 1.198(13) yes O138 . C139 . 1.219(11) yes O140 . C139 . 1.338(11) yes O140 . C141 . 1.459(11) yes C1 . C13 . 1.536(14) yes C1 . C139 . 1.493(14) yes C1 . H12 . 0.973 no C1 . H11 . 0.988 no C2 . C3 . 1.523(12) yes C2 . H21 . 0.982 no C2 . H22 . 0.977 no C3 . C4 . 1.521(12) yes C3 . H32 . 0.953 no C3 . H31 . 0.964 no C4 . C5 . 1.501(12) yes C4 . H42 . 0.962 no C4 . H41 . 0.966 no C8 . C12 . 1.507(12) yes C10 . C11 . 1.514(12) yes C10 . H101 . 0.970 no C10 . H102 . 0.982 no C11 . C12 . 1.519(12) yes C11 . H112 . 0.986 no C11 . H111 . 0.976 no C12 . H122 . 0.966 no C12 . H121 . 0.971 no C13 . C141 . 1.518(13) yes C13 . H131 . 0.957 no C13 . H132 . 0.963 no C17 . C30 . 1.588(11) yes C17 . H171 . 0.980 no C22 . C23 . 1.559(11) yes C22 . H221 . 0.973 no C23 . H231 . 0.981 no C28 . C32 . 1.566(10) yes C28 . H281 . 0.975 no C30 . H301 . 0.982 no C32 . H321 . 0.973 no C46 . C59 . 1.549(11) yes C46 . H461 . 0.973 no C51 . C61 . 1.578(11) yes C51 . H511 . 0.976 no C56 . C57 . 1.594(11) yes C56 . H561 . 0.980 no C57 . H571 . 0.980 no C59 . H591 . 0.958 no C60 . C135 . 1.377(19) yes C60 . C136 . 1.587(19) yes C60 . H601 . 0.950 no C60 . H602 . 0.950 no C61 . H611 . 0.984 no C142 . C135 . 1.60(2) yes C142 . C136 . 1.45(2) yes C142 . H1422 . 0.967 no C142 . H1421 . 0.969 no C77 . C90 . 1.576(11) yes C77 . H771 . 0.991 no C82 . C92 . 1.563(10) yes C82 . H821 . 0.985 no C87 . C88 . 1.583(11) yes C87 . H871 . 0.980 no C88 . H881 . 0.983 no C90 . H901 . 0.975 no C92 . H921 . 0.978 no C107 . C114 . 1.574(11) yes C107 . H1071 . 0.980 no C112 . C122 . 1.595(11) yes C112 . H1121 . 0.979 no C114 . H1141 . 0.980 no C119 . C120 . 1.576(10) yes C119 . H1191 . 0.993 no C120 . H1201 . 0.979 no C122 . H1221 . 0.971 no C134 . C135 . 1.531(13) yes C134 . H1342 . 0.968 no C134 . H1341 . 0.972 no C135 . H1351 . 0.950 no C135 . H1352 . 0.950 no C141 . H1412 . 0.964 no C141 . H1411 . 0.981 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 N16 . N14 . O13 . 116.8(7) yes N16 . N14 . O15 . 114.7(7) yes O13 . N14 . O15 . 128.3(8) yes N14 . N16 . C17 . 117.4(6) yes N14 . N16 . C23 . 116.3(6) yes C17 . N16 . C23 . 107.3(6) yes N19 . N18 . C17 . 117.6(6) yes N19 . N18 . C22 . 116.8(6) yes C17 . N18 . C22 . 107.2(6) yes N18 . N19 . O20 . 117.7(7) yes N18 . N19 . O21 . 115.2(7) yes O20 . N19 . O21 . 126.9(8) yes N25 . N24 . C23 . 116.9(6) yes N25 . N24 . C28 . 114.4(6) yes C23 . N24 . C28 . 117.1(6) yes N24 . N25 . O26 . 114.6(7) yes N24 . N25 . O27 . 118.1(7) yes O26 . N25 . O27 . 127.3(8) yes N40 . N29 . C28 . 111.5(6) yes N40 . N29 . C30 . 113.5(6) yes C28 . N29 . C30 . 106.0(6) yes N37 . N31 . C30 . 119.8(6) yes N37 . N31 . C32 . 120.0(6) yes C30 . N31 . C32 . 109.9(6) yes N34 . N33 . C22 . 118.9(6) yes N34 . N33 . C32 . 119.7(6) yes C22 . N33 . C32 . 116.7(6) yes N33 . N34 . O35 . 116.0(6) yes N33 . N34 . O36 . 116.2(6) yes O35 . N34 . O36 . 127.7(7) yes N31 . N37 . O38 . 115.6(6) yes N31 . N37 . O39 . 116.3(6) yes O38 . N37 . O39 . 128.0(7) yes N29 . N40 . O41 . 117.9(6) yes N29 . N40 . O42 . 115.5(7) yes O41 . N40 . O42 . 126.5(7) yes O43 . N44 . N45 . 116.5(7) yes O43 . N44 . O72 . 126.5(7) yes N45 . N44 . O72 . 117.0(7) yes N48 . N47 . C46 . 116.3(6) yes N48 . N47 . C51 . 115.3(6) yes C46 . N47 . C51 . 115.5(6) yes N47 . N48 . O49 . 115.3(7) yes N47 . N48 . O50 . 117.7(7) yes O49 . N48 . O50 . 127.0(8) yes N53 . N52 . C51 . 115.3(6) yes N53 . N52 . C56 . 114.9(6) yes C51 . N52 . C56 . 107.3(6) yes N52 . N53 . O54 . 117.3(6) yes N52 . N53 . O55 . 116.3(7) yes O54 . N53 . O55 . 126.3(7) yes N69 . N58 . C57 . 120.4(6) yes N69 . N58 . C59 . 120.8(6) yes C57 . N58 . C59 . 110.6(6) yes N66 . N60 . C59 . 120.0(6) yes N66 . N60 . C61 . 119.0(6) yes C59 . N60 . C61 . 116.7(6) yes N63 . N62 . C56 . 118.0(6) yes N63 . N62 . C61 . 119.0(6) yes C56 . N62 . C61 . 107.8(6) yes N62 . N63 . O64 . 115.7(7) yes N62 . N63 . O65 . 116.6(7) yes O64 . N63 . O65 . 127.7(7) yes N60 . N66 . O67 . 116.8(6) yes N60 . N66 . O68 . 116.2(6) yes O67 . N66 . O68 . 126.9(7) yes N58 . N69 . O70 . 116.4(7) yes N58 . N69 . O71 . 116.8(7) yes O70 . N69 . O71 . 126.8(7) yes N76 . N74 . O73 . 116.6(7) yes N76 . N74 . O75 . 116.8(7) yes O73 . N74 . O75 . 126.4(7) yes N74 . N76 . C77 . 119.0(6) yes N74 . N76 . C88 . 118.5(6) yes C77 . N76 . C88 . 107.8(6) yes N79 . N78 . C77 . 119.5(6) yes N79 . N78 . C82 . 121.0(6) yes C77 . N78 . C82 . 116.6(6) yes N78 . N79 . O80 . 117.0(6) yes N78 . N79 . O81 . 115.6(6) yes O80 . N79 . O81 . 127.3(7) yes N84 . N83 . C82 . 119.5(6) yes N84 . N83 . C87 . 119.9(6) yes C82 . N83 . C87 . 110.5(6) yes N83 . N84 . O85 . 116.7(7) yes N83 . N84 . O86 . 116.6(7) yes O85 . N84 . O86 . 126.7(7) yes N100 . N89 . C88 . 116.2(6) yes N100 . N89 . C90 . 114.8(6) yes C88 . N89 . C90 . 105.8(6) yes N97 . N91 . C90 . 117.2(6) yes N97 . N91 . C92 . 115.7(6) yes C90 . N91 . C92 . 117.0(6) yes N94 . N93 . C87 . 115.6(6) yes N94 . N93 . C92 . 113.1(6) yes C87 . N93 . C92 . 106.2(6) yes N93 . N94 . O95 . 116.9(7) yes N93 . N94 . O96 . 115.9(7) yes O95 . N94 . O96 . 127.0(7) yes N91 . N97 . O98 . 115.6(7) yes N91 . N97 . O99 . 116.5(7) yes O98 . N97 . O99 . 127.9(7) yes N89 . N100 . O101 . 116.5(7) yes N89 . N100 . O102 . 117.6(7) yes O101 . N100 . O102 . 125.7(7) yes N106 . N104 . O103 . 117.0(7) yes N106 . N104 . O105 . 115.8(7) yes O103 . N104 . O105 . 127.2(7) yes N104 . N106 . C107 . 115.7(6) yes N104 . N106 . C120 . 116.3(6) yes C107 . N106 . C120 . 116.6(6) yes N109 . N108 . C107 . 117.3(6) yes N109 . N108 . C112 . 118.9(6) yes C107 . N108 . C112 . 107.3(6) yes N108 . N109 . O110 . 115.2(6) yes N108 . N109 . O111 . 117.5(7) yes O110 . N109 . O111 . 127.0(7) yes N130 . N113 . C112 . 118.2(6) yes N130 . N113 . C114 . 115.5(6) yes C112 . N113 . C114 . 107.5(6) yes N116 . N115 . C114 . 119.5(6) yes N116 . N115 . C119 . 117.5(6) yes C114 . N115 . C119 . 117.5(6) yes N115 . N116 . O117 . 117.2(6) yes N115 . N116 . O118 . 114.5(6) yes O117 . N116 . O118 . 128.2(7) yes N127 . N121 . C120 . 111.7(6) yes N127 . N121 . C122 . 112.0(6) yes C120 . N121 . C122 . 106.8(6) yes N124 . N123 . C119 . 119.1(6) yes N124 . N123 . C122 . 120.4(6) yes C119 . N123 . C122 . 110.7(6) yes N123 . N124 . O125 . 115.5(6) yes N123 . N124 . O126 . 118.0(7) yes O125 . N124 . O126 . 126.5(7) yes N121 . N127 . O128 . 117.8(6) yes N121 . N127 . O129 . 115.3(7) yes O128 . N127 . O129 . 126.7(7) yes N113 . N130 . O131 . 116.3(7) yes N113 . N130 . O132 . 115.9(7) yes O131 . N130 . O132 . 127.7(7) yes C2 . O1 . C5 . 110.8(6) yes C8 . O9 . C10 . 110.0(6) yes N44 . N45 . C46 . 115.2(6) yes N44 . N45 . C57 . 116.1(6) yes C46 . N45 . C57 . 106.3(6) yes C134 . O133 . C136 . 111.2(7) yes C139 . O140 . C141 . 110.5(7) yes C13 . C1 . C139 . 102.4(8) yes C13 . C1 . H12 . 109.7 no C139 . C1 . H12 . 112.1 no C13 . C1 . H11 . 110.9 no C139 . C1 . H11 . 112.6 no H12 . C1 . H11 . 109.0 no O1 . C2 . C3 . 105.9(7) yes O1 . C2 . H21 . 111.6 no C3 . C2 . H21 . 110.4 no O1 . C2 . H22 . 107.6 no C3 . C2 . H22 . 111.3 no H21 . C2 . H22 . 110.0 no C2 . C3 . C4 . 101.9(7) yes C2 . C3 . H32 . 111.5 no C4 . C3 . H32 . 111.5 no C2 . C3 . H31 . 110.4 no C4 . C3 . H31 . 110.3 no H32 . C3 . H31 . 111.0 no C3 . C4 . C5 . 104.7(7) yes C3 . C4 . H42 . 109.1 no C5 . C4 . H42 . 110.9 no C3 . C4 . H41 . 111.9 no C5 . C4 . H41 . 111.0 no H42 . C4 . H41 . 109.2 no C4 . C5 . O1 . 109.3(7) yes C4 . C5 . O6 . 129.0(8) yes O1 . C5 . O6 . 121.7(7) yes O9 . C8 . O7 . 120.3(8) yes O9 . C8 . C12 . 110.6(7) yes O7 . C8 . C12 . 129.1(8) yes O9 . C10 . C11 . 105.2(6) yes O9 . C10 . H101 . 108.7 no C11 . C10 . H101 . 110.4 no O9 . C10 . H102 . 110.9 no C11 . C10 . H102 . 111.1 no H101 . C10 . H102 . 110.4 no C10 . C11 . C12 . 103.0(7) yes C10 . C11 . H112 . 111.3 no C12 . C11 . H112 . 111.8 no C10 . C11 . H111 . 110.7 no C12 . C11 . H111 . 111.4 no H112 . C11 . H111 . 108.7 no C11 . C12 . C8 . 103.0(7) yes C11 . C12 . H122 . 112.8 no C8 . C12 . H122 . 110.4 no C11 . C12 . H121 . 112.9 no C8 . C12 . H121 . 108.4 no H122 . C12 . H121 . 109.2 no C1 . C13 . C141 . 103.7(8) yes C1 . C13 . H131 . 111.1 no C141 . C13 . H131 . 112.4 no C1 . C13 . H132 . 107.4 no C141 . C13 . H132 . 109.6 no H131 . C13 . H132 . 112.3 no N18 . C17 . N16 . 104.9(6) yes N18 . C17 . C30 . 106.0(6) yes N16 . C17 . C30 . 109.4(6) yes N18 . C17 . H171 . 111.2 no N16 . C17 . H171 . 112.5 no C30 . C17 . H171 . 112.4 no N18 . C22 . N33 . 108.8(6) yes N18 . C22 . C23 . 104.0(6) yes N33 . C22 . C23 . 108.2(6) yes N18 . C22 . H221 . 112.2 no N33 . C22 . H221 . 111.7 no C23 . C22 . H221 . 111.6 no C22 . C23 . N16 . 106.2(6) yes C22 . C23 . N24 . 108.1(6) yes N16 . C23 . N24 . 110.9(6) yes C22 . C23 . H231 . 108.6 no N16 . C23 . H231 . 111.7 no N24 . C23 . H231 . 111.1 no N29 . C28 . N24 . 111.2(6) yes N29 . C28 . C32 . 105.8(6) yes N24 . C28 . C32 . 107.3(6) yes N29 . C28 . H281 . 110.4 no N24 . C28 . H281 . 110.9 no C32 . C28 . H281 . 111.0 no C17 . C30 . N31 . 113.9(6) yes C17 . C30 . N29 . 110.9(6) yes N31 . C30 . N29 . 99.7(6) yes C17 . C30 . H301 . 110.7 no N31 . C30 . H301 . 111.4 no N29 . C30 . H301 . 109.8 no C28 . C32 . N31 . 100.4(6) yes C28 . C32 . N33 . 108.8(6) yes N31 . C32 . N33 . 115.0(6) yes C28 . C32 . H321 . 113.7 no N31 . C32 . H321 . 109.3 no N33 . C32 . H321 . 109.6 no N45 . C46 . N47 . 111.2(6) yes N45 . C46 . C59 . 106.7(6) yes N47 . C46 . C59 . 108.9(6) yes N45 . C46 . H461 . 109.9 no N47 . C46 . H461 . 109.3 no C59 . C46 . H461 . 110.8 no N47 . C51 . N52 . 111.9(6) yes N47 . C51 . C61 . 108.1(6) yes N52 . C51 . C61 . 104.9(6) yes N47 . C51 . H511 . 109.5 no N52 . C51 . H511 . 111.5 no C61 . C51 . H511 . 110.7 no N62 . C56 . N52 . 104.3(6) yes N62 . C56 . C57 . 107.3(6) yes N52 . C56 . C57 . 109.1(6) yes N62 . C56 . H561 . 112.4 no N52 . C56 . H561 . 112.9 no C57 . C56 . H561 . 110.6 no C56 . C57 . N45 . 111.0(6) yes C56 . C57 . N58 . 112.0(6) yes N45 . C57 . N58 . 99.4(6) yes C56 . C57 . H571 . 110.5 no N45 . C57 . H571 . 111.4 no N58 . C57 . H571 . 112.1 no C46 . C59 . N58 . 100.5(6) yes C46 . C59 . N60 . 108.6(6) yes N58 . C59 . N60 . 113.2(6) yes C46 . C59 . H591 . 112.9 no N58 . C59 . H591 . 111.9 no N60 . C59 . H591 . 109.5 no C135 . C60 . C136 . 105.5(12) yes C135 . C60 . H601 . 110.4 no C136 . C60 . H601 . 110.5 no C135 . C60 . H602 . 110.5 no C136 . C60 . H602 . 110.5 no H601 . C60 . H602 . 109.5 no C51 . C61 . N62 . 104.3(6) yes C51 . C61 . N60 . 108.2(6) yes N62 . C61 . N60 . 110.7(6) yes C51 . C61 . H611 . 112.7 no N62 . C61 . H611 . 109.6 no N60 . C61 . H611 . 111.2 no C135 . C142 . C136 . 101.4(12) yes C135 . C142 . H1422 . 112.0 no C136 . C142 . H1422 . 112.1 no C135 . C142 . H1421 . 111.0 no C136 . C142 . H1421 . 110.3 no H1422 . C142 . H1421 . 109.8 no N76 . C77 . N78 . 110.1(6) yes N76 . C77 . C90 . 104.2(6) yes N78 . C77 . C90 . 108.4(6) yes N76 . C77 . H771 . 113.0 no N78 . C77 . H771 . 110.5 no C90 . C77 . H771 . 110.4 no N83 . C82 . N78 . 114.3(6) yes N83 . C82 . C92 . 100.2(6) yes N78 . C82 . C92 . 109.5(6) yes N83 . C82 . H821 . 111.2 no N78 . C82 . H821 . 109.5 no C92 . C82 . H821 . 111.9 no N93 . C87 . N83 . 99.7(6) yes N93 . C87 . C88 . 110.3(6) yes N83 . C87 . C88 . 113.3(6) yes N93 . C87 . H871 . 110.8 no N83 . C87 . H871 . 110.7 no C88 . C87 . H871 . 111.5 no C87 . C88 . N89 . 110.2(6) yes C87 . C88 . N76 . 107.3(6) yes N89 . C88 . N76 . 105.2(6) yes C87 . C88 . H881 . 111.0 no N89 . C88 . H881 . 111.8 no N76 . C88 . H881 . 111.0 no C77 . C90 . N89 . 104.9(6) yes C77 . C90 . N91 . 108.6(6) yes N89 . C90 . N91 . 111.8(6) yes C77 . C90 . H901 . 111.4 no N89 . C90 . H901 . 110.4 no N91 . C90 . H901 . 109.6 no C82 . C92 . N93 . 105.8(6) yes C82 . C92 . N91 . 107.7(6) yes N93 . C92 . N91 . 110.2(6) yes C82 . C92 . H921 . 111.7 no N93 . C92 . H921 . 109.8 no N91 . C92 . H921 . 111.5 no N108 . C107 . N106 . 110.9(6) yes N108 . C107 . C114 . 104.4(6) yes N106 . C107 . C114 . 108.7(6) yes N108 . C107 . H1071 . 109.9 no N106 . C107 . H1071 . 112.3 no C114 . C107 . H1071 . 110.4 no N113 . C112 . N108 . 105.5(6) yes N113 . C112 . C122 . 107.6(6) yes N108 . C112 . C122 . 109.8(6) yes N113 . C112 . H1121 . 109.4 no N108 . C112 . H1121 . 112.1 no C122 . C112 . H1121 . 112.1 no C107 . C114 . N113 . 104.0(6) yes C107 . C114 . N115 . 107.3(6) yes N113 . C114 . N115 . 110.0(6) yes C107 . C114 . H1141 . 112.3 no N113 . C114 . H1141 . 111.7 no N115 . C114 . H1141 . 111.3 no N123 . C119 . N115 . 114.7(6) yes N123 . C119 . C120 . 100.6(6) yes N115 . C119 . C120 . 107.0(6) yes N123 . C119 . H1191 . 111.5 no N115 . C119 . H1191 . 111.4 no C120 . C119 . H1191 . 111.2 no N121 . C120 . C119 . 104.8(6) yes N121 . C120 . N106 . 111.7(6) yes C119 . C120 . N106 . 109.0(6) yes N121 . C120 . H1201 . 110.3 no C119 . C120 . H1201 . 109.9 no N106 . C120 . H1201 . 110.8 no C112 . C122 . N123 . 112.6(6) yes C112 . C122 . N121 . 108.9(6) yes N123 . C122 . N121 . 100.5(6) yes C112 . C122 . H1221 . 110.6 no N123 . C122 . H1221 . 110.0 no N121 . C122 . H1221 . 113.9 no O133 . C134 . C135 . 105.5(7) yes O133 . C134 . H1342 . 110.7 no C135 . C134 . H1342 . 110.6 no O133 . C134 . H1341 . 108.8 no C135 . C134 . H1341 . 110.5 no H1342 . C134 . H1341 . 110.6 no C134 . C135 . C60 . 102.9(10) yes C134 . C135 . H1351 . 111.0 no C60 . C135 . H1351 . 111.0 no C134 . C135 . H1352 . 111.1 no C60 . C135 . H1352 . 111.2 no H1351 . C135 . H1352 . 109.5 no C60 . C136 . O133 . 103.0(10) yes C60 . C136 . O137 . 133.3(11) yes O133 . C136 . O137 . 119.9(10) yes C1 . C139 . O140 . 111.7(8) yes C1 . C139 . O138 . 126.5(9) yes O140 . C139 . O138 . 121.6(9) yes C13 . C141 . O140 . 105.3(7) yes C13 . C141 . H1412 . 108.8 no O140 . C141 . H1412 . 110.3 no C13 . C141 . H1411 . 113.4 no O140 . C141 . H1411 . 108.3 no H1412 . C141 . H1411 . 110.7 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 C1 . H12 . O27 . 142 0.97 2.54 3.356(12) yes C1 . H11 . O131 . 146 0.99 2.48 3.347(12) yes C2 . H21 . O49 3_565 126 0.98 2.45 3.130(12) yes C2 . H22 . O67 . 122 0.98 2.42 3.053(12) yes C10 . H101 . O20 . 120 0.97 2.59 3.190(12) yes C10 . H101 . O80 . 125 0.97 2.39 3.057(12) yes C10 . H102 . O105 . 137 0.98 2.45 3.243(12) yes C13 . H132 . O129 2_445 121 0.96 2.45 3.052(12) yes C17 . H171 . O9 . 140 0.98 2.32 3.128(12) yes C23 . H231 . O54 1_455 121 0.98 2.47 3.093(12) yes C28 . H281 . O118 3_565 157 0.97 2.29 3.215(12) yes C30 . H301 . O7 . 166 0.98 2.55 3.507(12) yes C32 . H321 . O132 3_565 155 0.97 2.29 3.201(12) yes C51 . H511 . O81 2_545 162 0.98 2.59 3.533(12) yes C57 . H571 . O133 . 139 0.98 2.34 3.149(12) yes C87 . H871 . O140 4_565 135 0.98 2.41 3.184(12) yes C112 . H1121 . O1 3_564 142 0.98 2.29 3.122(12) yes C119 . H1191 . O21 4_564 146 0.99 2.33 3.207(12) yes C120 . H1201 . O36 4_564 154 0.98 2.26 3.164(12) yes C122 . H1221 . O6 3_564 163 0.97 2.47 3.416(12) yes C134 . H1342 . O117 4_565 121 0.97 2.46 3.066(12) yes C134 . H1341 . O99 4_564 124 0.97 2.49 3.138(12) yes C141 . H1412 . O26 . 142 0.96 2.44 3.257(12) yes C135 . H1351 . O42 2_555 135 0.95 2.39 3.133(12) yes data_1 _database_code_depnum_ccdc_archive 'CCDC 832147' #TrackingRef '- cl20hmpa-Oct11.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 18.8930(3) _cell_length_b 12.07295(13) _cell_length_c 21.8241(4) _cell_angle_alpha 90 _cell_angle_beta 114.977(2) _cell_angle_gamma 90 _cell_volume 4512.41(14) _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' O 0.0492 0.0322 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' P 0.2955 0.4335 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' _cell_formula_units_Z 4 # Given Formula = C5.65 H14.12 N4.94 O3.53 P0.71 # Dc = 1.44 Fooo = 2064.00 Mu = 19.53 M = 975.79 # Found Formula = C5.65 H14.12 N4.94 O3.53 P0.71 # Dc = 1.44 FOOO = 2064.00 Mu = 19.53 M = 975.79 _chemical_formula_sum 'C24 H60 N21 O15 P3' _chemical_formula_moiety 'C24 H60 N21 O15 P3' _chemical_compound_source ? _chemical_formula_weight 229.60 _cell_measurement_reflns_used 23790 _cell_measurement_theta_min 2 _cell_measurement_theta_max 73 _cell_measurement_temperature 100 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.105 _exptl_crystal_size_max 0.351 _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 1.953 # Sheldrick geometric approximatio 0.81 0.89 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis PRO (Oxford Diffraction)' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.89 _diffrn_measurement_device 'Oxford Diffraction Supernova' _diffrn_measurement_device_type 'Atlas CCD' _diffrn_radiation_monochromator graphite _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)' _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction)' _computing_data_reduction 'CrysAlis PRO (Oxford Diffraction)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 43599 _reflns_number_total 8920 _diffrn_reflns_av_R_equivalents 0.067 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 8920 # Theoretical number of reflections is about 18167 _diffrn_reflns_theta_min 2.580 _diffrn_reflns_theta_max 73.440 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 70.502 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -23 _reflns_limit_h_max 21 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _oxford_diffrn_Wilson_B_factor 2.36 _oxford_diffrn_Wilson_scale 0.19 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.49 _refine_diff_density_max 0.64 # 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>-10.0\s(I) _refine_ls_number_reflns 8920 _refine_ls_number_restraints 0 _refine_ls_number_parameters 568 _oxford_refine_ls_R_factor_ref 0.0535 _refine_ls_wR_factor_ref 0.1370 _refine_ls_goodness_of_fit_ref 1.0187 _refine_ls_shift/su_max 0.0011371 _refine_ls_shift/su_mean 8.0992365 # The values computed from all data _oxford_reflns_number_all 8920 _refine_ls_R_factor_all 0.0535 _refine_ls_wR_factor_all 0.1370 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7321 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_gt 0.1329 # 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 none # 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^) + ( 0.11P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 P1 P 0.09884(3) 0.18905(4) 0.59544(2) 0.0227 1.0000 Uani . . . . . . . O2 O 0.14746(9) 0.15424(13) 0.56073(7) 0.0299 1.0000 Uani . . . . . . . N3 N 0.03303(10) 0.09553(14) 0.58928(9) 0.0258 1.0000 Uani . . . . . . . C4 C -0.03949(13) 0.11404(19) 0.59648(12) 0.0324 1.0000 Uani . . . . . . . C5 C 0.05292(14) -0.02135(17) 0.59157(12) 0.0316 1.0000 Uani . . . . . . . N6 N 0.04211(11) 0.30037(15) 0.56570(10) 0.0302 1.0000 Uani . . . . . . . C7 C -0.01740(15) 0.2966(2) 0.49544(12) 0.0371 1.0000 Uani . . . . . . . C8 C 0.07676(16) 0.4094(2) 0.58481(16) 0.0449 1.0000 Uani . . . . . . . N9 N 0.15484(10) 0.21341(15) 0.67577(9) 0.0272 1.0000 Uani . . . . . . . C10 C 0.23501(13) 0.2519(2) 0.69895(13) 0.0366 1.0000 Uani . . . . . . . C11 C 0.12147(15) 0.2313(2) 0.72405(11) 0.0365 1.0000 Uani . . . . . . . P12 P 0.18086(3) -0.28840(4) 0.32362(2) 0.0204 1.0000 Uani . . . . . . . O13 O 0.20667(9) -0.19254(12) 0.37050(7) 0.0275 1.0000 Uani . . . . . . . N14 N 0.25694(11) -0.35826(15) 0.32814(10) 0.0306 1.0000 Uani . . . . . . . C15 C 0.24913(17) -0.4633(2) 0.29225(14) 0.0419 1.0000 Uani . . . . . . . C16 C 0.33481(16) -0.3091(3) 0.35466(18) 0.0545 1.0000 Uani . . . . . . . N17 N 0.12782(10) -0.25954(14) 0.24276(8) 0.0254 1.0000 Uani . . . . . . . C18 C 0.16640(14) -0.23292(19) 0.19902(11) 0.0317 1.0000 Uani . . . . . . . C19 C 0.05838(13) -0.1913(2) 0.22739(12) 0.0340 1.0000 Uani . . . . . . . N20 N 0.12193(11) -0.36862(14) 0.34192(9) 0.0267 1.0000 Uani . . . . . . . C21 C 0.06561(15) -0.4463(2) 0.29609(13) 0.0385 1.0000 Uani . . . . . . . C22 C 0.14702(17) -0.3981(2) 0.41292(12) 0.0391 1.0000 Uani . . . . . . . P23 P 0.39799(3) 0.43221(4) 0.64653(3) 0.0240 1.0000 Uani . . . . . . . O24 O 0.35699(9) 0.33514(12) 0.60540(8) 0.0307 1.0000 Uani . . . . . . . N25 N 0.33269(10) 0.51837(14) 0.65173(9) 0.0271 1.0000 Uani . . . . . . . C26 C 0.35722(13) 0.62132(17) 0.69071(11) 0.0298 1.0000 Uani . . . . . . . C27 C 0.26034(17) 0.5320(3) 0.59255(16) 0.0598 1.0000 Uani . . . . . . . N28 N 0.45845(11) 0.41428(15) 0.72625(10) 0.0308 1.0000 Uani . . . . . . . C29 C 0.53736(14) 0.3722(2) 0.74516(15) 0.0444 1.0000 Uani . . . . . . . C30 C 0.42769(16) 0.3799(2) 0.77467(12) 0.0405 1.0000 Uani . . . . . . . N31 N 0.45360(14) 0.48950(18) 0.61450(12) 0.0406 1.0000 Uani . . . . . . . C32 C 0.50351(16) 0.5848(2) 0.64440(16) 0.0439 1.0000 Uani . . . . . . . C33 C 0.4408(3) 0.4674(4) 0.54632(18) 0.0742 1.0000 Uani . . . . . . . O34 O 0.12110(9) 0.27522(12) 0.42676(8) 0.0318 1.0000 Uani . . . . . . . N35 N 0.13136(10) 0.18511(15) 0.40664(9) 0.0281 1.0000 Uani . . . . . . . O36 O 0.08601(10) 0.13570(14) 0.35658(9) 0.0413 1.0000 Uani . . . . . . . N37 N 0.20126(9) 0.13073(13) 0.44547(8) 0.0202 1.0000 Uani . . . . . . . C38 C 0.26389(11) 0.18942(16) 0.49828(9) 0.0204 1.0000 Uani . . . . . . . N39 N 0.32752(10) 0.21722(14) 0.47907(8) 0.0230 1.0000 Uani . . . . . . . N40 N 0.31236(11) 0.27724(15) 0.42162(9) 0.0299 1.0000 Uani . . . . . . . O41 O 0.25280(10) 0.33226(14) 0.39947(8) 0.0373 1.0000 Uani . . . . . . . O42 O 0.36162(10) 0.27131(15) 0.39869(9) 0.0388 1.0000 Uani . . . . . . . C43 C 0.38546(11) 0.12893(16) 0.49800(10) 0.0227 1.0000 Uani . . . . . . . N44 N 0.38670(9) 0.09590(14) 0.56242(8) 0.0219 1.0000 Uani . . . . . . . C45 C 0.30706(11) 0.10793(16) 0.55873(9) 0.0206 1.0000 Uani . . . . . . . N46 N 0.26808(9) 0.00271(13) 0.54251(8) 0.0200 1.0000 Uani . . . . . . . N47 N 0.25620(10) -0.05778(15) 0.59155(8) 0.0244 1.0000 Uani . . . . . . . O48 O 0.21950(9) -0.14413(13) 0.57313(8) 0.0308 1.0000 Uani . . . . . . . O49 O 0.28164(10) -0.01786(14) 0.64805(7) 0.0330 1.0000 Uani . . . . . . . C50 C 0.26082(11) -0.05085(16) 0.48127(9) 0.0194 1.0000 Uani . . . . . . . C51 C 0.22041(11) 0.03050(15) 0.42036(9) 0.0206 1.0000 Uani . . . . . . . N52 N 0.28005(10) 0.05310(14) 0.39441(8) 0.0231 1.0000 Uani . . . . . . . C53 C 0.35617(11) 0.02654(16) 0.44724(10) 0.0222 1.0000 Uani . . . . . . . N54 N 0.33662(9) -0.06862(13) 0.47830(8) 0.0211 1.0000 Uani . . . . . . . N55 N 0.39479(10) -0.12419(15) 0.52899(9) 0.0271 1.0000 Uani . . . . . . . O56 O 0.46160(9) -0.10976(15) 0.53437(8) 0.0357 1.0000 Uani . . . . . . . O57 O 0.37545(10) -0.18521(14) 0.56408(8) 0.0353 1.0000 Uani . . . . . . . N58 N 0.26232(12) 0.00596(15) 0.32950(9) 0.0295 1.0000 Uani . . . . . . . O59 O 0.19509(10) 0.01477(13) 0.28873(7) 0.0347 1.0000 Uani . . . . . . . O60 O 0.31657(11) -0.03137(16) 0.32000(9) 0.0414 1.0000 Uani . . . . . . . N61 N 0.44910(10) 0.13656(15) 0.62190(9) 0.0278 1.0000 Uani . . . . . . . O62 O 0.50682(9) 0.16902(16) 0.61619(9) 0.0397 1.0000 Uani . . . . . . . O63 O 0.44016(10) 0.12668(13) 0.67341(7) 0.0331 1.0000 Uani . . . . . . . H501 H 0.2325 -0.1197 0.4746 0.0232 1.0000 Uiso R . . . . . . H451 H 0.3090 0.1337 0.6005 0.0237 1.0000 Uiso R . . . . . . H511 H 0.1749 -0.0012 0.3851 0.0237 1.0000 Uiso R . . . . . . H531 H 0.3932 0.0063 0.4296 0.0266 1.0000 Uiso R . . . . . . H41 H -0.0814 0.0831 0.5581 0.0492 1.0000 Uiso R . . . . . . H43 H -0.0362 0.0798 0.6377 0.0490 1.0000 Uiso R . . . . . . H42 H -0.0488 0.1920 0.5973 0.0494 1.0000 Uiso R . . . . . . H51 H 0.0090 -0.0616 0.5589 0.0479 1.0000 Uiso R . . . . . . H53 H 0.0650 -0.0509 0.6357 0.0482 1.0000 Uiso R . . . . . . H52 H 0.0970 -0.0299 0.5815 0.0482 1.0000 Uiso R . . . . . . H71 H -0.0588 0.3511 0.4892 0.0571 1.0000 Uiso R . . . . . . H72 H -0.0410 0.2222 0.4854 0.0583 1.0000 Uiso R . . . . . . H73 H 0.0075 0.3156 0.4660 0.0579 1.0000 Uiso R . . . . . . H81 H 0.0363 0.4629 0.5817 0.0700 1.0000 Uiso R . . . . . . H82 H 0.1156 0.4102 0.6311 0.0688 1.0000 Uiso R . . . . . . H83 H 0.1019 0.4316 0.5551 0.0703 1.0000 Uiso R . . . . . . H102 H 0.2700 0.2128 0.7396 0.0557 1.0000 Uiso R . . . . . . H101 H 0.2389 0.3303 0.7087 0.0555 1.0000 Uiso R . . . . . . H103 H 0.2521 0.2395 0.6648 0.0558 1.0000 Uiso R . . . . . . H111 H 0.1551 0.2035 0.7675 0.0559 1.0000 Uiso R . . . . . . H113 H 0.0727 0.1923 0.7097 0.0560 1.0000 Uiso R . . . . . . H112 H 0.1122 0.3097 0.7283 0.0559 1.0000 Uiso R . . . . . . H151 H 0.2827 -0.5171 0.3227 0.0620 1.0000 Uiso R . . . . . . H153 H 0.1962 -0.4911 0.2742 0.0626 1.0000 Uiso R . . . . . . H152 H 0.2643 -0.4537 0.2555 0.0623 1.0000 Uiso R . . . . . . H161 H 0.3721 -0.3616 0.3832 0.0843 1.0000 Uiso R . . . . . . H162 H 0.3379 -0.2428 0.3805 0.0846 1.0000 Uiso R . . . . . . H163 H 0.3477 -0.2913 0.3169 0.0847 1.0000 Uiso R . . . . . . H181 H 0.1316 -0.2472 0.1524 0.0486 1.0000 Uiso R . . . . . . H182 H 0.2123 -0.2778 0.2094 0.0485 1.0000 Uiso R . . . . . . H183 H 0.1809 -0.1558 0.2026 0.0482 1.0000 Uiso R . . . . . . H192 H 0.0226 -0.1976 0.1805 0.0503 1.0000 Uiso R . . . . . . H191 H 0.0324 -0.2161 0.2544 0.0505 1.0000 Uiso R . . . . . . H193 H 0.0711 -0.1144 0.2373 0.0514 1.0000 Uiso R . . . . . . H211 H 0.0184 -0.4423 0.3030 0.0586 1.0000 Uiso R . . . . . . H213 H 0.0857 -0.5200 0.3064 0.0585 1.0000 Uiso R . . . . . . H212 H 0.0531 -0.4286 0.2497 0.0585 1.0000 Uiso R . . . . . . H221 H 0.1012 -0.4051 0.4220 0.0601 1.0000 Uiso R . . . . . . H223 H 0.1738 -0.4683 0.4214 0.0598 1.0000 Uiso R . . . . . . H222 H 0.1826 -0.3439 0.4426 0.0602 1.0000 Uiso R . . . . . . H261 H 0.3181 0.6423 0.7058 0.0464 1.0000 Uiso R . . . . . . H262 H 0.4065 0.6127 0.7301 0.0452 1.0000 Uiso R . . . . . . H263 H 0.3612 0.6800 0.6620 0.0455 1.0000 Uiso R . . . . . . H271 H 0.2194 0.5560 0.6049 0.0910 1.0000 Uiso R . . . . . . H272 H 0.2660 0.5878 0.5623 0.0917 1.0000 Uiso R . . . . . . H273 H 0.2443 0.4628 0.5691 0.0904 1.0000 Uiso R . . . . . . H292 H 0.5737 0.4038 0.7874 0.0666 1.0000 Uiso R . . . . . . H291 H 0.5536 0.3925 0.7098 0.0664 1.0000 Uiso R . . . . . . H293 H 0.5388 0.2928 0.7486 0.0668 1.0000 Uiso R . . . . . . H301 H 0.4606 0.4053 0.8201 0.0619 1.0000 Uiso R . . . . . . H303 H 0.3762 0.4114 0.7627 0.0616 1.0000 Uiso R . . . . . . H302 H 0.4232 0.2990 0.7759 0.0618 1.0000 Uiso R . . . . . . H321 H 0.5529 0.5737 0.6410 0.0668 1.0000 Uiso R . . . . . . H323 H 0.5151 0.5918 0.6916 0.0671 1.0000 Uiso R . . . . . . H322 H 0.4797 0.6513 0.6208 0.0669 1.0000 Uiso R . . . . . . H331 H 0.4906 0.4652 0.5429 0.1121 1.0000 Uiso R . . . . . . H332 H 0.4147 0.3974 0.5308 0.1126 1.0000 Uiso R . . . . . . H333 H 0.4062 0.5267 0.5169 0.1111 1.0000 Uiso R . . . . . . H381 H 0.2433 0.2548 0.5125 0.0239 1.0000 Uiso R . . . . . . H431 H 0.4377 0.1568 0.5028 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 P1 0.0243(3) 0.0234(2) 0.0215(2) 0.00136(18) 0.0107(2) 0.00314(19) O2 0.0305(8) 0.0353(8) 0.0284(7) 0.0015(6) 0.0169(6) 0.0040(6) N3 0.0245(8) 0.0253(8) 0.0266(8) 0.0001(7) 0.0096(7) 0.0050(7) C4 0.0242(10) 0.0349(11) 0.0361(11) -0.0008(9) 0.0107(9) 0.0001(9) C5 0.0376(12) 0.0257(10) 0.0333(11) -0.0001(8) 0.0167(9) 0.0027(9) N6 0.0347(10) 0.0258(9) 0.0312(9) 0.0038(7) 0.0150(8) 0.0046(7) C7 0.0417(13) 0.0395(12) 0.0321(11) 0.0089(9) 0.0175(10) 0.0133(10) C8 0.0430(14) 0.0272(11) 0.0611(17) 0.0090(11) 0.0188(13) -0.0023(10) N9 0.0269(9) 0.0310(9) 0.0241(8) -0.0019(7) 0.0112(7) -0.0044(7) C10 0.0279(11) 0.0415(12) 0.0388(12) -0.0082(10) 0.0125(10) -0.0041(10) C11 0.0395(12) 0.0468(13) 0.0265(10) -0.0096(9) 0.0171(10) -0.0144(10) P12 0.0212(2) 0.0206(2) 0.0195(2) -0.00216(17) 0.00875(19) -0.00148(18) O13 0.0310(8) 0.0250(7) 0.0225(7) -0.0056(5) 0.0073(6) -0.0050(6) N14 0.0299(9) 0.0295(9) 0.0353(9) 0.0032(7) 0.0164(8) 0.0028(8) C15 0.0588(16) 0.0300(11) 0.0511(15) 0.0050(10) 0.0369(13) 0.0108(11) C16 0.0280(13) 0.0593(17) 0.074(2) -0.0020(15) 0.0188(13) 0.0029(12) N17 0.0258(8) 0.0274(8) 0.0223(8) -0.0014(7) 0.0096(7) -0.0015(7) C18 0.0415(12) 0.0311(10) 0.0256(10) -0.0027(8) 0.0170(9) -0.0043(9) C19 0.0225(10) 0.0394(12) 0.0316(11) 0.0023(9) 0.0031(9) 0.0009(9) N20 0.0317(9) 0.0278(8) 0.0243(8) -0.0026(7) 0.0153(7) -0.0046(7) C21 0.0416(13) 0.0352(12) 0.0420(13) -0.0040(10) 0.0208(11) -0.0124(10) C22 0.0560(15) 0.0364(12) 0.0318(12) 0.0019(9) 0.0251(11) -0.0031(11) P23 0.0240(3) 0.0220(2) 0.0255(3) -0.00401(18) 0.0100(2) -0.00214(19) O24 0.0354(8) 0.0274(7) 0.0278(7) -0.0062(6) 0.0119(6) -0.0048(6) N25 0.0229(8) 0.0248(8) 0.0269(9) -0.0029(7) 0.0041(7) 0.0012(7) C26 0.0296(11) 0.0235(9) 0.0329(11) -0.0035(8) 0.0099(9) 0.0033(8) C27 0.0393(15) 0.0530(17) 0.0551(17) -0.0167(14) -0.0111(13) 0.0123(13) N28 0.0244(9) 0.0241(8) 0.0373(10) -0.0030(7) 0.0067(8) 0.0024(7) C29 0.0257(11) 0.0354(12) 0.0554(15) -0.0060(11) 0.0010(11) 0.0060(10) C30 0.0452(14) 0.0427(13) 0.0249(11) 0.0034(9) 0.0064(10) 0.0030(11) N31 0.0483(12) 0.0384(11) 0.0469(12) -0.0087(9) 0.0315(10) -0.0120(9) C32 0.0372(13) 0.0355(12) 0.0651(17) -0.0002(12) 0.0275(13) -0.0066(10) C33 0.102(3) 0.086(3) 0.0564(19) -0.0184(18) 0.055(2) -0.037(2) O34 0.0302(8) 0.0272(7) 0.0343(8) 0.0063(6) 0.0100(6) 0.0081(6) N35 0.0210(8) 0.0279(9) 0.0295(9) 0.0086(7) 0.0047(7) 0.0013(7) O36 0.0261(8) 0.0358(9) 0.0394(9) 0.0025(7) -0.0082(7) -0.0009(7) N37 0.0161(7) 0.0231(8) 0.0178(7) 0.0025(6) 0.0038(6) 0.0025(6) C38 0.0196(9) 0.0238(9) 0.0166(8) 0.0012(7) 0.0065(7) 0.0005(7) N39 0.0233(8) 0.0242(8) 0.0214(8) 0.0003(6) 0.0092(7) -0.0025(6) N40 0.0324(10) 0.0308(9) 0.0254(9) 0.0017(7) 0.0112(8) -0.0087(8) O41 0.0375(9) 0.0373(8) 0.0336(8) 0.0147(7) 0.0115(7) 0.0032(7) O42 0.0391(9) 0.0484(10) 0.0364(9) 0.0065(7) 0.0232(7) -0.0069(8) C43 0.0196(9) 0.0263(9) 0.0219(9) -0.0027(7) 0.0084(7) -0.0025(7) N44 0.0173(8) 0.0279(8) 0.0161(7) -0.0038(6) 0.0029(6) -0.0008(6) C45 0.0194(9) 0.0244(9) 0.0162(8) -0.0006(7) 0.0058(7) 0.0025(7) N46 0.0235(8) 0.0236(7) 0.0148(7) 0.0010(6) 0.0100(6) 0.0010(6) N47 0.0218(8) 0.0332(9) 0.0195(8) 0.0058(7) 0.0098(7) 0.0047(7) O48 0.0326(8) 0.0327(8) 0.0303(8) 0.0061(6) 0.0164(6) -0.0032(6) O49 0.0356(8) 0.0459(9) 0.0178(7) 0.0048(6) 0.0114(6) 0.0033(7) C50 0.0185(9) 0.0222(8) 0.0171(8) -0.0003(7) 0.0072(7) -0.0002(7) C51 0.0208(9) 0.0231(9) 0.0159(8) 0.0006(7) 0.0059(7) -0.0024(7) N52 0.0267(8) 0.0274(8) 0.0157(7) -0.0028(6) 0.0096(7) -0.0039(7) C53 0.0228(9) 0.0262(9) 0.0207(9) -0.0024(7) 0.0123(8) -0.0012(7) N54 0.0187(8) 0.0246(8) 0.0194(7) -0.0012(6) 0.0075(6) 0.0008(6) N55 0.0238(8) 0.0320(9) 0.0256(8) 0.0007(7) 0.0106(7) 0.0059(7) O56 0.0218(7) 0.0482(10) 0.0379(8) 0.0004(7) 0.0134(7) 0.0075(7) O57 0.0337(8) 0.0390(9) 0.0340(8) 0.0123(7) 0.0150(7) 0.0098(7) N58 0.0434(11) 0.0290(9) 0.0182(8) -0.0039(7) 0.0150(8) -0.0118(8) O59 0.0456(10) 0.0329(8) 0.0169(7) 0.0002(6) 0.0047(7) -0.0093(7) O60 0.0485(10) 0.0528(10) 0.0344(9) -0.0148(8) 0.0287(8) -0.0123(8) N61 0.0225(9) 0.0281(8) 0.0232(8) -0.0038(7) 0.0004(7) 0.0015(7) O62 0.0198(7) 0.0540(10) 0.0372(9) -0.0091(8) 0.0043(7) -0.0095(7) O63 0.0354(8) 0.0359(8) 0.0177(7) -0.0010(6) 0.0011(6) 0.0012(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.214(17) 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 P1 . O2 . 1.4770(15) yes P1 . N3 . 1.6424(18) yes P1 . N6 . 1.6699(19) yes P1 . N9 . 1.6470(18) yes N3 . C4 . 1.461(3) yes N3 . C5 . 1.456(3) yes C4 . H41 . 0.953 no C4 . H43 . 0.968 no C4 . H42 . 0.959 no C5 . H51 . 0.966 no C5 . H53 . 0.961 no C5 . H52 . 0.953 no N6 . C7 . 1.470(3) yes N6 . C8 . 1.451(3) yes C7 . H71 . 0.986 no C7 . H72 . 0.986 no C7 . H73 . 0.970 no C8 . H81 . 0.981 no C8 . H82 . 0.965 no C8 . H83 . 0.988 no N9 . C10 . 1.456(3) yes N9 . C11 . 1.454(3) yes C10 . H102 . 0.975 no C10 . H101 . 0.966 no C10 . H103 . 0.942 no C11 . H111 . 0.952 no C11 . H113 . 0.962 no C11 . H112 . 0.973 no P12 . O13 . 1.4841(14) yes P12 . N14 . 1.6332(19) yes P12 . N17 . 1.6572(17) yes P12 . N20 . 1.6470(17) yes N14 . C15 . 1.464(3) yes N14 . C16 . 1.460(3) yes C15 . H151 . 0.954 no C15 . H153 . 0.967 no C15 . H152 . 0.967 no C16 . H161 . 0.957 no C16 . H162 . 0.967 no C16 . H163 . 0.977 no N17 . C18 . 1.461(3) yes N17 . C19 . 1.463(3) yes C18 . H181 . 0.966 no C18 . H182 . 0.964 no C18 . H183 . 0.964 no C19 . H192 . 0.963 no C19 . H191 . 0.960 no C19 . H193 . 0.960 no N20 . C21 . 1.454(3) yes N20 . C22 . 1.460(3) yes C21 . H211 . 0.968 no C21 . H213 . 0.957 no C21 . H212 . 0.962 no C22 . H221 . 0.970 no C22 . H223 . 0.964 no C22 . H222 . 0.966 no P23 . O24 . 1.4806(15) yes P23 . N25 . 1.6539(18) yes P23 . N28 . 1.643(2) yes P23 . N31 . 1.641(2) yes N25 . C26 . 1.466(3) yes N25 . C27 . 1.440(3) yes C26 . H261 . 0.961 no C26 . H262 . 0.970 no C26 . H263 . 0.970 no C27 . H271 . 0.965 no C27 . H272 . 0.981 no C27 . H273 . 0.959 no N28 . C29 . 1.460(3) yes N28 . C30 . 1.465(3) yes C29 . H292 . 0.966 no C29 . H291 . 0.975 no C29 . H293 . 0.961 no C30 . H301 . 0.971 no C30 . H303 . 0.972 no C30 . H302 . 0.981 no N31 . C32 . 1.456(3) yes N31 . C33 . 1.428(4) yes C32 . H321 . 0.976 no C32 . H323 . 0.963 no C32 . H322 . 0.957 no C33 . H331 . 0.975 no C33 . H332 . 0.965 no C33 . H333 . 0.999 no O34 . N35 . 1.219(2) yes N35 . O36 . 1.222(2) yes N35 . N37 . 1.396(2) yes N37 . C38 . 1.442(2) yes N37 . C51 . 1.436(2) yes C38 . N39 . 1.469(2) yes C38 . C45 . 1.570(2) yes C38 . H381 . 0.986 no N39 . N40 . 1.370(2) yes N39 . C43 . 1.457(3) yes N40 . O41 . 1.217(3) yes N40 . O42 . 1.231(2) yes C43 . N44 . 1.452(2) yes C43 . C53 . 1.595(3) yes C43 . H431 . 1.005 no N44 . C45 . 1.480(2) yes N44 . N61 . 1.423(2) yes C45 . N46 . 1.436(2) yes C45 . H451 . 0.948 no N46 . N47 . 1.390(2) yes N46 . C50 . 1.438(2) yes N47 . O48 . 1.222(2) yes N47 . O49 . 1.218(2) yes C50 . C51 . 1.568(2) yes C50 . N54 . 1.476(2) yes C50 . H501 . 0.966 no C51 . N52 . 1.485(2) yes C51 . H511 . 0.959 no N52 . C53 . 1.449(3) yes N52 . N58 . 1.429(2) yes C53 . N54 . 1.459(2) yes C53 . H531 . 0.961 no N54 . N55 . 1.362(2) yes N55 . O56 . 1.230(2) yes N55 . O57 . 1.224(2) yes N58 . O59 . 1.209(3) yes N58 . O60 . 1.215(3) yes N61 . O62 . 1.214(2) yes N61 . O63 . 1.211(2) yes 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 O2 . P1 . N3 . 112.06(9) yes O2 . P1 . N6 . 117.76(9) yes N3 . P1 . N6 . 100.49(9) yes O2 . P1 . N9 . 109.73(9) yes N3 . P1 . N9 . 109.49(9) yes N6 . P1 . N9 . 106.76(10) yes P1 . N3 . C4 . 126.73(15) yes P1 . N3 . C5 . 119.22(15) yes C4 . N3 . C5 . 112.63(18) yes N3 . C4 . H41 . 108.4 no N3 . C4 . H43 . 109.9 no H41 . C4 . H43 . 110.6 no N3 . C4 . H42 . 109.9 no H41 . C4 . H42 . 108.1 no H43 . C4 . H42 . 109.9 no N3 . C5 . H51 . 109.5 no N3 . C5 . H53 . 110.0 no H51 . C5 . H53 . 108.7 no N3 . C5 . H52 . 109.6 no H51 . C5 . H52 . 109.6 no H53 . C5 . H52 . 109.4 no P1 . N6 . C7 . 117.59(15) yes P1 . N6 . C8 . 118.75(17) yes C7 . N6 . C8 . 112.41(19) yes N6 . C7 . H71 . 109.6 no N6 . C7 . H72 . 109.6 no H71 . C7 . H72 . 108.7 no N6 . C7 . H73 . 108.2 no H71 . C7 . H73 . 109.3 no H72 . C7 . H73 . 111.5 no N6 . C8 . H81 . 109.5 no N6 . C8 . H82 . 111.2 no H81 . C8 . H82 . 107.0 no N6 . C8 . H83 . 109.9 no H81 . C8 . H83 . 110.6 no H82 . C8 . H83 . 108.6 no P1 . N9 . C10 . 122.23(15) yes P1 . N9 . C11 . 121.17(15) yes C10 . N9 . C11 . 113.98(18) yes N9 . C10 . H102 . 111.6 no N9 . C10 . H101 . 111.1 no H102 . C10 . H101 . 108.3 no N9 . C10 . H103 . 109.2 no H102 . C10 . H103 . 108.4 no H101 . C10 . H103 . 108.1 no N9 . C11 . H111 . 110.9 no N9 . C11 . H113 . 109.8 no H111 . C11 . H113 . 107.3 no N9 . C11 . H112 . 111.3 no H111 . C11 . H112 . 108.7 no H113 . C11 . H112 . 108.7 no O13 . P12 . N14 . 109.66(10) yes O13 . P12 . N17 . 116.42(9) yes N14 . P12 . N17 . 107.09(9) yes O13 . P12 . N20 . 110.51(9) yes N14 . P12 . N20 . 110.45(9) yes N17 . P12 . N20 . 102.43(9) yes P12 . N14 . C15 . 121.83(17) yes P12 . N14 . C16 . 121.87(18) yes C15 . N14 . C16 . 114.9(2) yes N14 . C15 . H151 . 109.3 no N14 . C15 . H153 . 111.8 no H151 . C15 . H153 . 108.4 no N14 . C15 . H152 . 110.0 no H151 . C15 . H152 . 108.4 no H153 . C15 . H152 . 108.8 no N14 . C16 . H161 . 109.3 no N14 . C16 . H162 . 111.7 no H161 . C16 . H162 . 108.7 no N14 . C16 . H163 . 108.8 no H161 . C16 . H163 . 108.7 no H162 . C16 . H163 . 109.5 no P12 . N17 . C18 . 119.87(15) yes P12 . N17 . C19 . 116.29(14) yes C18 . N17 . C19 . 111.89(18) yes N17 . C18 . H181 . 110.1 no N17 . C18 . H182 . 111.7 no H181 . C18 . H182 . 107.0 no N17 . C18 . H183 . 111.3 no H181 . C18 . H183 . 107.6 no H182 . C18 . H183 . 109.1 no N17 . C19 . H192 . 111.0 no N17 . C19 . H191 . 108.9 no H192 . C19 . H191 . 108.4 no N17 . C19 . H193 . 112.3 no H192 . C19 . H193 . 108.2 no H191 . C19 . H193 . 107.8 no P12 . N20 . C21 . 125.85(15) yes P12 . N20 . C22 . 116.80(16) yes C21 . N20 . C22 . 112.86(18) yes N20 . C21 . H211 . 108.4 no N20 . C21 . H213 . 109.6 no H211 . C21 . H213 . 108.1 no N20 . C21 . H212 . 111.3 no H211 . C21 . H212 . 108.8 no H213 . C21 . H212 . 110.5 no N20 . C22 . H221 . 108.7 no N20 . C22 . H223 . 109.1 no H221 . C22 . H223 . 108.9 no N20 . C22 . H222 . 111.6 no H221 . C22 . H222 . 110.5 no H223 . C22 . H222 . 107.9 no O24 . P23 . N25 . 108.96(9) yes O24 . P23 . N28 . 119.30(9) yes N25 . P23 . N28 . 102.44(9) yes O24 . P23 . N31 . 109.92(10) yes N25 . P23 . N31 . 113.24(11) yes N28 . P23 . N31 . 102.87(11) yes P23 . N25 . C26 . 120.71(14) yes P23 . N25 . C27 . 117.60(17) yes C26 . N25 . C27 . 111.81(19) yes N25 . C26 . H261 . 108.8 no N25 . C26 . H262 . 111.9 no H261 . C26 . H262 . 108.3 no N25 . C26 . H263 . 109.6 no H261 . C26 . H263 . 108.0 no H262 . C26 . H263 . 110.1 no N25 . C27 . H271 . 110.6 no N25 . C27 . H272 . 110.5 no H271 . C27 . H272 . 108.1 no N25 . C27 . H273 . 110.3 no H271 . C27 . H273 . 107.5 no H272 . C27 . H273 . 109.8 no P23 . N28 . C29 . 121.04(18) yes P23 . N28 . C30 . 119.40(16) yes C29 . N28 . C30 . 111.5(2) yes N28 . C29 . H292 . 111.2 no N28 . C29 . H291 . 108.3 no H292 . C29 . H291 . 108.9 no N28 . C29 . H293 . 111.2 no H292 . C29 . H293 . 109.5 no H291 . C29 . H293 . 107.7 no N28 . C30 . H301 . 111.6 no N28 . C30 . H303 . 110.6 no H301 . C30 . H303 . 106.7 no N28 . C30 . H302 . 111.5 no H301 . C30 . H302 . 108.1 no H303 . C30 . H302 . 108.0 no P23 . N31 . C32 . 123.53(18) yes P23 . N31 . C33 . 120.6(2) yes C32 . N31 . C33 . 114.0(2) yes N31 . C32 . H321 . 108.4 no N31 . C32 . H323 . 111.2 no H321 . C32 . H323 . 107.5 no N31 . C32 . H322 . 110.7 no H321 . C32 . H322 . 108.7 no H323 . C32 . H322 . 110.2 no N31 . C33 . H331 . 110.0 no N31 . C33 . H332 . 111.4 no H331 . C33 . H332 . 108.5 no N31 . C33 . H333 . 108.1 no H331 . C33 . H333 . 111.2 no H332 . C33 . H333 . 107.6 no O34 . N35 . O36 . 126.84(18) yes O34 . N35 . N37 . 117.05(17) yes O36 . N35 . N37 . 116.08(17) yes N35 . N37 . C38 . 120.06(15) yes N35 . N37 . C51 . 119.40(16) yes C38 . N37 . C51 . 117.72(15) yes N37 . C38 . N39 . 112.23(15) yes N37 . C38 . C45 . 108.88(15) yes N39 . C38 . C45 . 100.70(14) yes N37 . C38 . H381 . 110.2 no N39 . C38 . H381 . 112.6 no C45 . C38 . H381 . 111.8 no C38 . N39 . N40 . 120.13(16) yes C38 . N39 . C43 . 111.05(15) yes N40 . N39 . C43 . 119.22(16) yes N39 . N40 . O41 . 116.94(17) yes N39 . N40 . O42 . 116.09(18) yes O41 . N40 . O42 . 126.95(18) yes N39 . C43 . N44 . 100.29(15) yes N39 . C43 . C53 . 111.79(15) yes N44 . C43 . C53 . 108.58(15) yes N39 . C43 . H431 . 111.8 no N44 . C43 . H431 . 112.2 no C53 . C43 . H431 . 111.7 no C43 . N44 . C45 . 108.67(15) yes C43 . N44 . N61 . 117.21(16) yes C45 . N44 . N61 . 116.59(15) yes C38 . C45 . N44 . 105.22(14) yes C38 . C45 . N46 . 108.48(15) yes N44 . C45 . N46 . 109.30(15) yes C38 . C45 . H451 . 113.4 no N44 . C45 . H451 . 110.7 no N46 . C45 . H451 . 109.6 no C45 . N46 . N47 . 120.52(15) yes C45 . N46 . C50 . 117.69(15) yes N47 . N46 . C50 . 119.75(15) yes N46 . N47 . O48 . 116.66(16) yes N46 . N47 . O49 . 116.65(17) yes O48 . N47 . O49 . 126.67(17) yes N46 . C50 . C51 . 109.12(15) yes N46 . C50 . N54 . 113.11(15) yes C51 . C50 . N54 . 100.83(14) yes N46 . C50 . H501 . 110.9 no C51 . C50 . H501 . 111.7 no N54 . C50 . H501 . 110.8 no C50 . C51 . N37 . 108.37(14) yes C50 . C51 . N52 . 105.21(15) yes N37 . C51 . N52 . 110.17(15) yes C50 . C51 . H511 . 112.4 no N37 . C51 . H511 . 110.9 no N52 . C51 . H511 . 109.6 no C51 . N52 . C53 . 108.29(14) yes C51 . N52 . N58 . 114.01(15) yes C53 . N52 . N58 . 116.06(16) yes C43 . C53 . N52 . 108.54(15) yes C43 . C53 . N54 . 111.68(15) yes N52 . C53 . N54 . 100.55(15) yes C43 . C53 . H531 . 112.1 no N52 . C53 . H531 . 112.5 no N54 . C53 . H531 . 110.8 no C50 . N54 . C53 . 110.29(15) yes C50 . N54 . N55 . 120.06(15) yes C53 . N54 . N55 . 119.32(16) yes N54 . N55 . O56 . 116.83(17) yes N54 . N55 . O57 . 116.93(17) yes O56 . N55 . O57 . 126.22(19) yes N52 . N58 . O59 . 115.35(18) yes N52 . N58 . O60 . 117.08(18) yes O59 . N58 . O60 . 127.37(18) yes N44 . N61 . O62 . 116.87(17) yes N44 . N61 . O63 . 115.24(17) yes O62 . N61 . O63 . 127.64(18) 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 C15 . H152 . O49 4_544 163 0.97 2.52 3.459(4) yes C30 . H303 . O60 4_555 135 0.97 2.47 3.238(4) yes C43 . H431 . O56 2_656 139 1.00 2.43 3.260(4) yes _chemical_name_common 2,4,6,8,10,12-hexanitrohexaazisowurtzitane: