data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Colin R. Pulham' 'Adam Cumming' 'Duncan J. Francis' 'William G. Marshall' 'David I. A. Millar' 'Iain Oswald' 'Colin R. Pulham' _publ_contact_author_name 'Colin R. Pulham' _publ_contact_author_email C.R.PULHAM@ED.AC.UK _publ_section_title ; The crystal structure of ?-RDX - an elusive form of an explosive revealed ; # Attachment 'RDX_150K.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 705290' _audit_creation_date 08-08-28 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 'david in Pca2(1)' _chemical_name_systematic Beta-1,3,5-trinitrohexahydro-1,3,5-triazine _chemical_melting_point ? _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # 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)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 15.1267(11) _cell_length_b 7.4563(6) _cell_length_c 14.3719(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1621.0(2) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21 ' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y,z+1/2 x+1/2,-y,z -x,-y,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 8 # Given Formula = C3 H6 N6 O6 # Dc = 1.82 Fooo = 912.00 Mu = 1.73 M = 444.23 # Found Formula = C3 H6 N6 O6 # Dc = 1.82 FOOO = 912.00 Mu = 1.73 M = 444.23 _chemical_formula_sum 'C3 H6 N6 O6' _chemical_formula_moiety 'C3 H6 N6 O6' _chemical_compound_source ? _chemical_formula_weight 222.12 _cell_measurement_reflns_used 2888 _cell_measurement_theta_min 3 _cell_measurement_theta_max 24 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.38 _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.173 # Sheldrick geometric approximatio 0.96 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.97 _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 # 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 10899 _reflns_number_total 2097 _diffrn_reflns_av_R_equivalents 0.038 # Number of reflections with Friedels Law is 2097 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2040 _diffrn_reflns_theta_min 2.693 _diffrn_reflns_theta_max 28.425 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.856 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min 0 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 2.28 _oxford_diffrn_Wilson_scale 42.76 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.34 _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 2097 _refine_ls_number_restraints 1 _refine_ls_number_parameters 271 _oxford_refine_ls_R_factor_ref 0.0672 _refine_ls_wR_factor_ref 0.0912 _refine_ls_goodness_of_fit_ref 0.8136 _refine_ls_shift/su_max 0.000149 # The values computed from all data _oxford_reflns_number_all 2097 _refine_ls_R_factor_all 0.0672 _refine_ls_wR_factor_all 0.0912 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1491 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_gt 0.0847 # 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 constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.00P] ,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, G., 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. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: 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 C1 C 0.4904(2) 0.6676(6) 0.4504(3) 0.0269 1.0000 Uani . . . . . . . N11 N 0.5441(2) 0.7057(4) 0.5315(2) 0.0253 1.0000 Uani . . . . . . . N14 N 0.5073(2) 0.8303(5) 0.5942(3) 0.0372 1.0000 Uani . . . . . . . O18 O 0.4476(2) 0.9257(5) 0.5665(3) 0.0487 1.0000 Uani . . . . . . . O19 O 0.5400(2) 0.8395(6) 0.6703(3) 0.0649 1.0000 Uani . . . . . . . C2 C 0.5821(2) 0.5471(7) 0.5742(3) 0.0322 1.0000 Uani . . . . . . . N12 N 0.5158(3) 0.4108(5) 0.5927(3) 0.0397 1.0000 Uani . . . . . . . O20 O 0.5156(4) 0.4953(8) 0.7425(3) 0.0888 1.0000 Uani . . . . . . . O21 O 0.4111(3) 0.3214(6) 0.6897(4) 0.1035 1.0000 Uani . . . . . . . N15 N 0.4762(3) 0.4107(7) 0.6806(4) 0.0636 1.0000 Uani . . . . . . . C3 C 0.4598(3) 0.3693(6) 0.5141(4) 0.0463 1.0000 Uani . . . . . . . N10 N 0.4256(2) 0.5311(5) 0.4689(3) 0.0319 1.0000 Uani . . . . . . . N13 N 0.3399(2) 0.5863(6) 0.4896(3) 0.0442 1.0000 Uani . . . . . . . O16 O 0.31628(19) 0.7305(5) 0.4599(3) 0.0500 1.0000 Uani . . . . . . . O17 O 0.2945(2) 0.4838(6) 0.5331(4) 0.0974 1.0000 Uani . . . . . . . C4 C 0.7415(3) 0.0896(5) 0.2059(3) 0.0287 1.0000 Uani . . . . . . . N17 N 0.78958(19) -0.0359(4) 0.2649(2) 0.0276 1.0000 Uani . . . . . . . N20 N 0.8707(2) 0.0206(5) 0.3025(3) 0.0316 1.0000 Uani . . . . . . . O24 O 0.9050(2) 0.1524(4) 0.2673(2) 0.0447 1.0000 Uani . . . . . . . O25 O 0.90190(17) -0.0726(4) 0.3636(2) 0.0387 1.0000 Uani . . . . . . . C5 C 0.7353(2) -0.1563(5) 0.3206(3) 0.0254 1.0000 Uani . . . . . . . N18 N 0.6660(2) -0.0600(4) 0.3694(2) 0.0259 1.0000 Uani . . . . . . . N21 N 0.6800(2) -0.0141(5) 0.4628(2) 0.0274 1.0000 Uani . . . . . . . O26 O 0.7384(2) -0.0966(4) 0.5032(2) 0.0383 1.0000 Uani . . . . . . . O27 O 0.62981(18) 0.0937(4) 0.4983(2) 0.0339 1.0000 Uani . . . . . . . C6 C 0.6158(2) 0.0680(6) 0.3118(3) 0.0267 1.0000 Uani . . . . . . . N16 N 0.6732(2) 0.1852(4) 0.2580(2) 0.0266 1.0000 Uani . . . . . . . N19 N 0.6970(2) 0.3486(5) 0.2982(2) 0.0290 1.0000 Uani . . . . . . . O22 O 0.6496(2) 0.4043(4) 0.3603(2) 0.0363 1.0000 Uani . . . . . . . O23 O 0.7591(2) 0.4277(4) 0.2645(3) 0.0470 1.0000 Uani . . . . . . . H11 H 0.4615 0.7729 0.4280 0.0351 1.0000 Uiso R . . . . . . H12 H 0.5288 0.6175 0.4035 0.0342 1.0000 Uiso R . . . . . . H21 H 0.6146 0.5833 0.6300 0.0363 1.0000 Uiso R . . . . . . H22 H 0.6245 0.4977 0.5303 0.0365 1.0000 Uiso R . . . . . . H31 H 0.4962 0.3063 0.4699 0.0523 1.0000 Uiso R . . . . . . H32 H 0.4077 0.2977 0.5390 0.0527 1.0000 Uiso R . . . . . . H41 H 0.7814 0.1759 0.1766 0.0347 1.0000 Uiso R . . . . . . H42 H 0.7103 0.0186 0.1586 0.0347 1.0000 Uiso R . . . . . . H51 H 0.7727 -0.2182 0.3659 0.0322 1.0000 Uiso R . . . . . . H52 H 0.7066 -0.2416 0.2762 0.0314 1.0000 Uiso R . . . . . . H61 H 0.5787 0.1396 0.3511 0.0323 1.0000 Uiso R . . . . . . H62 H 0.5813 -0.0004 0.2677 0.0317 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 0.0276(19) 0.035(2) 0.0178(18) 0.0008(18) 0.0012(16) 0.0075(18) N11 0.0228(16) 0.0293(18) 0.0239(16) -0.0023(15) 0.0012(13) -0.0017(14) N14 0.0330(19) 0.037(2) 0.041(2) -0.015(2) 0.0069(18) -0.0124(17) O18 0.0466(19) 0.039(2) 0.061(2) -0.0096(18) 0.0146(18) 0.0090(17) O19 0.071(3) 0.077(3) 0.047(2) -0.036(2) -0.009(2) -0.013(2) C2 0.0190(18) 0.057(3) 0.0207(19) 0.004(2) -0.0021(16) 0.011(2) N12 0.037(2) 0.042(2) 0.040(2) 0.0177(19) 0.0148(18) 0.0193(19) O20 0.126(4) 0.098(4) 0.042(2) 0.031(3) 0.041(3) 0.051(3) O21 0.084(3) 0.077(3) 0.150(5) 0.069(3) 0.081(3) 0.029(3) N15 0.069(3) 0.060(3) 0.062(3) 0.040(3) 0.037(3) 0.040(3) C3 0.031(2) 0.027(2) 0.081(4) -0.001(3) 0.019(3) 0.0049(19) N10 0.0252(17) 0.0301(19) 0.040(2) -0.0143(18) -0.0042(16) 0.0034(15) N13 0.0248(18) 0.043(2) 0.065(3) -0.012(2) -0.0069(19) -0.0018(18) O16 0.0298(16) 0.050(2) 0.070(2) 0.001(2) -0.0103(17) 0.0137(16) O17 0.0288(19) 0.072(3) 0.192(6) 0.040(3) 0.032(3) -0.0037(18) C4 0.031(2) 0.034(2) 0.0211(19) -0.0025(18) 0.0043(17) 0.0055(19) N17 0.0234(15) 0.0332(19) 0.0262(17) -0.0109(16) 0.0026(15) -0.0004(14) N20 0.0243(17) 0.040(2) 0.0309(18) -0.0197(19) 0.0060(15) 0.0062(16) O24 0.0353(16) 0.0412(19) 0.058(2) -0.0152(18) 0.0071(17) -0.0117(15) O25 0.0240(14) 0.058(2) 0.0337(16) -0.0135(17) -0.0026(14) 0.0076(15) C5 0.025(2) 0.0211(19) 0.030(2) -0.0043(17) -0.0087(17) -0.0006(15) N18 0.0221(15) 0.0284(18) 0.0273(18) -0.0043(16) 0.0005(14) -0.0018(14) N21 0.0320(18) 0.0271(18) 0.0232(16) -0.0006(16) 0.0021(15) -0.0128(15) O26 0.0405(17) 0.0452(18) 0.0291(15) 0.0030(15) -0.0064(15) 0.0045(16) O27 0.0358(15) 0.0391(17) 0.0268(14) -0.0037(15) 0.0100(13) -0.0008(14) C6 0.0201(17) 0.032(2) 0.028(2) -0.0069(19) -0.0029(16) -0.0016(17) N16 0.0269(16) 0.0311(19) 0.0219(17) -0.0031(16) -0.0034(14) 0.0004(15) N19 0.0362(18) 0.0239(18) 0.0270(18) 0.0024(16) -0.0026(15) 0.0103(15) O22 0.0426(17) 0.0349(17) 0.0313(15) -0.0076(15) 0.0005(15) 0.0143(14) O23 0.0487(19) 0.0235(15) 0.069(2) 0.0033(19) 0.0167(19) 0.0003(15) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.17225(11) 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 . N11 . 1.449(5) yes C1 . N10 . 1.437(5) yes C1 . H11 . 0.955 no C1 . H12 . 0.965 no N11 . N14 . 1.409(5) yes N11 . C2 . 1.451(5) yes N14 . O18 . 1.217(5) yes N14 . O19 . 1.202(5) yes C2 . N12 . 1.453(6) yes C2 . H21 . 0.978 no C2 . H22 . 0.972 no N12 . N15 . 1.396(6) yes N12 . C3 . 1.446(7) yes O20 . N15 . 1.243(7) yes O21 . N15 . 1.196(6) yes C3 . N10 . 1.465(6) yes C3 . H31 . 0.963 no C3 . H32 . 1.017 no N10 . N13 . 1.392(5) yes N13 . O16 . 1.211(5) yes N13 . O17 . 1.203(5) yes C4 . N17 . 1.458(5) yes C4 . N16 . 1.461(5) yes C4 . H41 . 0.978 no C4 . H42 . 0.983 no N17 . N20 . 1.405(4) yes N17 . C5 . 1.456(5) yes N20 . O24 . 1.222(5) yes N20 . O25 . 1.215(5) yes C5 . N18 . 1.451(5) yes C5 . H51 . 0.979 no C5 . H52 . 0.999 no N18 . N21 . 1.401(4) yes N18 . C6 . 1.474(5) yes N21 . O26 . 1.223(4) yes N21 . O27 . 1.218(4) yes C6 . N16 . 1.454(5) yes C6 . H61 . 0.959 no C6 . H62 . 0.967 no N16 . N19 . 1.396(4) yes N19 . O22 . 1.219(4) yes N19 . O23 . 1.210(4) 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 N11 . C1 . N10 . 111.9(3) yes N11 . C1 . H11 . 111.5 no N10 . C1 . H11 . 109.4 no N11 . C1 . H12 . 107.5 no N10 . C1 . H12 . 105.4 no H11 . C1 . H12 . 111.0 no C1 . N11 . N14 . 115.0(3) yes C1 . N11 . C2 . 113.7(3) yes N14 . N11 . C2 . 115.0(3) yes N11 . N14 . O18 . 118.0(4) yes N11 . N14 . O19 . 117.2(4) yes O18 . N14 . O19 . 124.7(4) yes N11 . C2 . N12 . 112.0(3) yes N11 . C2 . H21 . 108.7 no N12 . C2 . H21 . 113.0 no N11 . C2 . H22 . 107.1 no N12 . C2 . H22 . 108.0 no H21 . C2 . H22 . 107.8 no C2 . N12 . N15 . 117.5(5) yes C2 . N12 . C3 . 114.3(3) yes N15 . N12 . C3 . 117.1(4) yes N12 . N15 . O20 . 116.2(5) yes N12 . N15 . O21 . 116.9(7) yes O20 . N15 . O21 . 126.7(6) yes N12 . C3 . N10 . 112.1(4) yes N12 . C3 . H31 . 106.6 no N10 . C3 . H31 . 108.1 no N12 . C3 . H32 . 107.0 no N10 . C3 . H32 . 108.3 no H31 . C3 . H32 . 114.8 no C3 . N10 . C1 . 115.1(3) yes C3 . N10 . N13 . 118.5(4) yes C1 . N10 . N13 . 117.7(3) yes N10 . N13 . O16 . 117.5(4) yes N10 . N13 . O17 . 117.1(4) yes O16 . N13 . O17 . 125.3(4) yes N17 . C4 . N16 . 111.6(3) yes N17 . C4 . H41 . 111.4 no N16 . C4 . H41 . 109.7 no N17 . C4 . H42 . 107.2 no N16 . C4 . H42 . 106.1 no H41 . C4 . H42 . 110.7 no C4 . N17 . N20 . 117.8(3) yes C4 . N17 . C5 . 115.7(3) yes N20 . N17 . C5 . 117.8(3) yes N17 . N20 . O24 . 117.0(4) yes N17 . N20 . O25 . 116.5(4) yes O24 . N20 . O25 . 126.4(4) yes N17 . C5 . N18 . 111.6(3) yes N17 . C5 . H51 . 109.3 no N18 . C5 . H51 . 109.2 no N17 . C5 . H52 . 106.7 no N18 . C5 . H52 . 108.0 no H51 . C5 . H52 . 112.0 no C5 . N18 . N21 . 118.4(3) yes C5 . N18 . C6 . 114.8(3) yes N21 . N18 . C6 . 117.2(3) yes N18 . N21 . O26 . 116.2(3) yes N18 . N21 . O27 . 117.9(3) yes O26 . N21 . O27 . 125.6(3) yes N18 . C6 . N16 . 112.4(3) yes N18 . C6 . H61 . 109.3 no N16 . C6 . H61 . 109.1 no N18 . C6 . H62 . 107.8 no N16 . C6 . H62 . 106.9 no H61 . C6 . H62 . 111.3 no C4 . N16 . C6 . 113.6(3) yes C4 . N16 . N19 . 117.1(3) yes C6 . N16 . N19 . 117.4(3) yes N16 . N19 . O22 . 116.6(3) yes N16 . N19 . O23 . 117.4(4) yes O22 . N19 . O23 . 125.8(4) yes # Attachment 'RDX_273K.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 705291' _audit_creation_date 08-10-03 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 'iain in Pca2(1)' _chemical_name_systematic Beta-1,3,5-trinitrohexahydro-1,3,5-triazine _chemical_melting_point ? _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # 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)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 15.0972(7) _cell_length_b 7.5463(4) _cell_length_c 14.4316(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1644.16(13) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21 ' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y,z+1/2 x+1/2,-y,z -x,-y,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 8 # Given Formula = C3 H6 N6 O6 # Dc = 1.79 Fooo = 912.00 Mu = 1.71 M = 444.23 # Found Formula = C3 H6 N6 O6 # Dc = 1.79 FOOO = 912.00 Mu = 1.71 M = 444.23 _chemical_formula_sum 'C3 H6 N6 O6' _chemical_formula_moiety 'C3 H6 N6 O6' _chemical_compound_source ? _chemical_formula_weight 222.12 _cell_measurement_reflns_used 2672 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 273 _exptl_crystal_description lathe _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.171 # Sheldrick geometric approximatio 0.99 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.67 _exptl_absorpt_correction_T_max 0.97 _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 # 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 273 _diffrn_reflns_number 10137 _reflns_number_total 1244 _diffrn_reflns_av_R_equivalents 0.055 # Number of reflections with Friedels Law is 1244 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1189 _diffrn_reflns_theta_min 2.699 _diffrn_reflns_theta_max 23.312 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 22.846 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min 0 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _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 -0.43 _refine_diff_density_max 0.52 # 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 1244 _refine_ls_number_restraints 277 _refine_ls_number_parameters 271 _oxford_refine_ls_R_factor_ref 0.0975 _refine_ls_wR_factor_ref 0.1405 _refine_ls_goodness_of_fit_ref 0.7647 _refine_ls_shift/su_max 0.000045 # The values computed from all data _oxford_reflns_number_all 1244 _refine_ls_R_factor_all 0.0975 _refine_ls_wR_factor_all 0.1405 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 588 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_gt 0.1292 # 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 constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.56P] ,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, G., 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. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: 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 O22 O 0.4074(6) 0.8647(11) 0.6193(7) 0.1219 1.0000 Uani D U . . . . . O23 O 0.4013(5) 1.0926(12) 0.5314(5) 0.1058 1.0000 Uani D U . . . . . O24 O 0.2358(5) 1.1051(9) 0.3980(5) 0.0931 1.0000 Uani D U . . . . . O25 O 0.1305(5) 0.9139(9) 0.4041(5) 0.0851 1.0000 Uani D U . . . . . O26 O 0.1481(5) 0.6076(8) 0.5380(5) 0.0850 1.0000 Uani D U . . . . . O27 O 0.2620(6) 0.5836(8) 0.6251(7) 0.1254 1.0000 Uani D U . . . . . C1 C 0.5404(7) 0.6374(12) 0.8693(8) 0.1106 1.0000 Uani D U . . . . . C2 C 0.4169(5) 0.4511(11) 0.8244(6) 0.0766 1.0000 Uani D U . . . . . C3 C 0.5201(6) 0.3525(14) 0.9412(6) 0.0913 1.0000 Uani D U . . . . . C4 C 0.2341(5) 1.1645(9) 0.5795(6) 0.0617 1.0000 Uani D U . . . . . C5 C 0.1175(5) 0.9378(10) 0.5880(5) 0.0613 1.0000 Uani D U . . . . . C6 C 0.2483(5) 0.9122(10) 0.6878(5) 0.0645 1.0000 Uani D U . . . . . N10 N 0.5830(6) 0.4883(12) 0.9149(7) 0.1094 1.0000 Uani D U . . . . . N11 N 0.4791(6) 0.5870(10) 0.7967(6) 0.0938 1.0000 Uani D U . . . . . N12 N 0.4621(5) 0.3021(9) 0.8663(5) 0.0699 1.0000 Uani D U . . . . . N16 N 0.2920(4) 1.0440(8) 0.6300(4) 0.0574 1.0000 Uani D U . . . . . N17 N 0.1644(4) 1.0675(9) 0.5313(5) 0.0582 1.0000 Uani D U . . . . . N18 N 0.1779(4) 0.8213(9) 0.6375(4) 0.0573 1.0000 Uani D U . . . . . N19 N 0.3715(6) 0.9971(11) 0.5902(6) 0.0728 1.0000 Uani D U . . . . . N20 N 0.1791(5) 1.0235(10) 0.4380(5) 0.0639 1.0000 Uani D U . . . . . N21 N 0.1986(5) 0.6625(10) 0.5956(5) 0.0669 1.0000 Uani D U . . . . . N15 N 0.4966(7) 0.1703(14) 0.8080(7) 0.1005 1.0000 Uani D U . . . . . N14 N 0.5112(9) 0.5764(18) 0.7060(9) 0.1479 1.0000 Uani D U . . . . . N13 N 0.6663(9) 0.4375(18) 0.8835(10) 0.1717 1.0000 Uani D U . . . . . O20 O 0.4621(7) 0.1545(16) 0.7344(7) 0.1670 1.0000 Uani D U . . . . . O21 O 0.5579(7) 0.0834(12) 0.8321(7) 0.1399 1.0000 Uani D U . . . . . O17 O 0.7023(7) 0.5451(19) 0.8366(13) 0.2643 1.0000 Uani D U . . . . . O18 O 0.5755(8) 0.6640(15) 0.6922(9) 0.2359 1.0000 Uani D U . . . . . O16 O 0.6904(7) 0.2954(18) 0.9106(10) 0.2278 1.0000 Uani D U . . . . . O19 O 0.4711(10) 0.482(2) 0.6534(6) 0.1940 1.0000 Uani D U . . . . . H11 H 0.5083 0.7078 0.9147 0.1363 1.0000 Uiso R . . . . . . H12 H 0.5871 0.7060 0.8395 0.1363 1.0000 Uiso R . . . . . . H21 H 0.3758 0.4967 0.8703 0.0963 1.0000 Uiso R . . . . . . H22 H 0.3839 0.4108 0.7705 0.0963 1.0000 Uiso R . . . . . . H31 H 0.4835 0.4001 0.9915 0.1125 1.0000 Uiso R . . . . . . H32 H 0.5522 0.2479 0.9605 0.1123 1.0000 Uiso R . . . . . . H41 H 0.2067 1.2461 0.6237 0.0792 1.0000 Uiso R . . . . . . H42 H 0.2696 1.2262 0.5347 0.0797 1.0000 Uiso R . . . . . . H51 H 0.0821 1.0008 0.6347 0.0765 1.0000 Uiso R . . . . . . H52 H 0.0797 0.8669 0.5481 0.0766 1.0000 Uiso R . . . . . . H61 H 0.2215 0.9732 0.7400 0.0812 1.0000 Uiso R . . . . . . H62 H 0.2912 0.8237 0.7089 0.0815 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 O22 0.098(6) 0.092(5) 0.175(8) -0.054(5) -0.001(6) 0.035(4) O23 0.074(5) 0.163(8) 0.081(5) -0.029(5) 0.025(4) -0.024(5) O24 0.096(6) 0.116(5) 0.067(4) 0.012(4) 0.014(4) -0.003(4) O25 0.100(5) 0.092(5) 0.063(4) -0.005(4) -0.025(4) 0.000(4) O26 0.097(5) 0.068(5) 0.090(5) -0.022(4) -0.002(4) -0.029(4) O27 0.144(8) 0.048(4) 0.185(9) 0.010(6) -0.056(6) 0.010(4) C1 0.085(7) 0.051(6) 0.195(9) -0.044(6) 0.045(6) -0.008(4) C2 0.039(6) 0.131(6) 0.059(5) -0.003(4) 0.000(4) 0.010(4) C3 0.125(7) 0.101(7) 0.048(5) -0.002(4) -0.008(4) 0.060(5) C4 0.070(5) 0.047(5) 0.068(5) -0.005(4) 0.008(4) -0.006(3) C5 0.050(5) 0.067(5) 0.067(5) -0.015(4) 0.006(3) -0.007(3) C6 0.074(5) 0.066(5) 0.054(5) -0.005(3) -0.009(3) -0.009(4) N10 0.076(5) 0.120(6) 0.132(7) -0.081(6) -0.028(5) 0.027(3) N11 0.095(6) 0.088(5) 0.099(5) 0.042(5) 0.040(4) 0.040(4) N12 0.087(6) 0.067(4) 0.056(4) -0.005(3) 0.031(3) -0.011(3) N16 0.050(3) 0.055(4) 0.068(4) -0.018(3) 0.003(3) -0.005(2) N17 0.050(4) 0.063(4) 0.061(3) -0.003(3) 0.002(3) 0.008(3) N18 0.060(4) 0.065(3) 0.047(4) -0.004(3) 0.010(3) -0.015(3) N19 0.057(4) 0.084(5) 0.078(6) -0.046(4) 0.006(4) -0.005(3) N20 0.067(6) 0.064(5) 0.061(3) -0.002(4) -0.002(3) 0.015(3) N21 0.078(6) 0.043(4) 0.080(6) 0.003(3) -0.002(3) -0.019(3) N15 0.128(9) 0.083(7) 0.091(6) -0.028(5) 0.056(5) -0.021(5) N14 0.165(11) 0.153(12) 0.126(6) 0.075(7) 0.091(7) 0.084(7) N13 0.071(7) 0.172(11) 0.272(15) -0.138(10) -0.021(8) 0.029(5) O20 0.162(9) 0.210(10) 0.129(8) -0.117(8) 0.030(6) -0.041(7) O21 0.164(9) 0.092(7) 0.164(8) -0.018(6) 0.081(6) 0.024(5) O17 0.076(8) 0.223(11) 0.49(3) -0.148(13) 0.077(10) -0.056(7) O18 0.236(13) 0.154(11) 0.318(15) 0.121(9) 0.212(12) 0.070(7) O16 0.145(10) 0.266(13) 0.272(14) -0.120(12) -0.089(9) 0.132(8) O19 0.265(15) 0.254(16) 0.063(5) 0.046(6) 0.036(8) 0.122(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1738(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O22 . N19 . 1.212(7) yes O23 . N19 . 1.200(7) yes O24 . N20 . 1.202(7) yes O25 . N20 . 1.209(7) yes O26 . N21 . 1.202(7) yes O27 . N21 . 1.205(7) yes C1 . N10 . 1.453(5) yes C1 . N11 . 1.449(5) yes C1 . H11 . 0.973 no C1 . H12 . 0.975 no C2 . N11 . 1.447(4) yes C2 . N12 . 1.448(4) yes C2 . H21 . 0.970 no C2 . H22 . 0.971 no C3 . N10 . 1.449(5) yes C3 . N12 . 1.441(4) yes C3 . H31 . 0.980 no C3 . H32 . 0.968 no C4 . N16 . 1.456(4) yes C4 . N17 . 1.458(4) yes C4 . H41 . 0.978 no C4 . H42 . 0.960 no C5 . N17 . 1.459(4) yes C5 . N18 . 1.454(4) yes C5 . H51 . 0.981 no C5 . H52 . 0.972 no C6 . N16 . 1.456(4) yes C6 . N18 . 1.458(4) yes C6 . H61 . 0.970 no C6 . H62 . 0.980 no N10 . N13 . 1.390(15) yes N11 . N14 . 1.397(15) yes N12 . N15 . 1.403(12) yes N16 . N19 . 1.378(9) yes N17 . N20 . 1.405(9) yes N18 . N21 . 1.378(9) yes N15 . O20 . 1.189(8) yes N15 . O21 . 1.186(8) yes N14 . O18 . 1.191(9) yes N14 . O19 . 1.206(8) yes N13 . O17 . 1.189(9) yes N13 . O16 . 1.198(8) 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 N10 . C1 . N11 . 114.0(8) yes N10 . C1 . H11 . 109.8 no N11 . C1 . H11 . 108.2 no N10 . C1 . H12 . 106.9 no N11 . C1 . H12 . 106.4 no H11 . C1 . H12 . 111.6 no N11 . C2 . N12 . 111.1(6) yes N11 . C2 . H21 . 110.6 no N12 . C2 . H21 . 106.9 no N11 . C2 . H22 . 109.4 no N12 . C2 . H22 . 109.4 no H21 . C2 . H22 . 109.4 no N10 . C3 . N12 . 112.9(7) yes N10 . C3 . H31 . 107.7 no N12 . C3 . H31 . 108.1 no N10 . C3 . H32 . 108.9 no N12 . C3 . H32 . 107.8 no H31 . C3 . H32 . 111.6 no N16 . C4 . N17 . 111.0(6) yes N16 . C4 . H41 . 108.7 no N17 . C4 . H41 . 108.8 no N16 . C4 . H42 . 107.8 no N17 . C4 . H42 . 109.0 no H41 . C4 . H42 . 111.6 no N17 . C5 . N18 . 112.1(6) yes N17 . C5 . H51 . 108.9 no N18 . C5 . H51 . 107.3 no N17 . C5 . H52 . 108.7 no N18 . C5 . H52 . 109.0 no H51 . C5 . H52 . 110.7 no N16 . C6 . N18 . 111.5(6) yes N16 . C6 . H61 . 108.0 no N18 . C6 . H61 . 107.9 no N16 . C6 . H62 . 110.1 no N18 . C6 . H62 . 108.4 no H61 . C6 . H62 . 110.9 no C1 . N10 . C3 . 112.1(9) yes C1 . N10 . N13 . 117.8(11) yes C3 . N10 . N13 . 118.9(10) yes C1 . N11 . C2 . 113.6(7) yes C1 . N11 . N14 . 118.1(10) yes C2 . N11 . N14 . 116.3(9) yes C2 . N12 . C3 . 113.2(7) yes C2 . N12 . N15 . 118.3(8) yes C3 . N12 . N15 . 114.3(8) yes C4 . N16 . C6 . 116.2(7) yes C4 . N16 . N19 . 118.3(7) yes C6 . N16 . N19 . 117.3(7) yes C5 . N17 . C4 . 114.8(7) yes C5 . N17 . N20 . 117.1(6) yes C4 . N17 . N20 . 117.5(7) yes C6 . N18 . C5 . 114.6(7) yes C6 . N18 . N21 . 117.6(7) yes C5 . N18 . N21 . 116.9(6) yes N16 . N19 . O22 . 117.2(9) yes N16 . N19 . O23 . 117.8(8) yes O22 . N19 . O23 . 124.9(11) yes N17 . N20 . O25 . 117.0(7) yes N17 . N20 . O24 . 116.8(7) yes O25 . N20 . O24 . 126.0(9) yes N18 . N21 . O27 . 117.0(8) yes N18 . N21 . O26 . 117.3(8) yes O27 . N21 . O26 . 125.4(9) yes N12 . N15 . O20 . 116.4(10) yes N12 . N15 . O21 . 120.4(10) yes O20 . N15 . O21 . 123.2(13) yes N11 . N14 . O18 . 114.1(13) yes N11 . N14 . O19 . 116.7(11) yes O18 . N14 . O19 . 129.3(16) yes N10 . N13 . O17 . 114.3(14) yes N10 . N13 . O16 . 114.6(14) yes O17 . N13 . O16 . 131.1(19) yes