Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'C. R. Pulham' _publ_contact_author_address ; School of Chemistry The University of Edinburgh King's Buildings West Mains Road Edinburgh SCOTLAND EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email C.R.PULHAM@ED.AC.UK _publ_section_title ; Explosives under pressure the crystal structure of ?-RDX as determined by high-pressure X-ray and neutron diffraction ; loop_ _publ_author_name 'C. R. Pulham' 'Adam Cumming' 'Alistair J. Davidson' 'Duncan J. Francis' 'Alistair Lennie' ; W.G.Marshall ; 'David I. A. Millar' 'Iain D. H. Oswald' 'John E. Warren' data_1 _database_code_depnum_ccdc_archive 'CCDC 659283' _pd_block_id 2007-08-09T16:55|AL_54TNS|al|Overall _audit_creation_method 'from EXP file using GSAS2CIF' _audit_creation_date 2007-08-09T16:55 _audit_author_name 'Davidson, Alistair J.' _audit_update_record ; 2007-08-09T16:55 Initial CIF as created by GSAS2CIF ; # The following items are used to identify the programs used. _computing_molecular_graphics GSAS _computing_publication_material GSAS _refine_ls_weighting_scheme calc _refine_ls_weighting_details calc _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_constraints 161 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? # 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA _pd_char_particle_morphology ? _chemical_name_systematic ; 'cyclotrimethylene-trinitramine' ; _chemical_name_common cyclotrimethylene-trinitramine _chemical_formula_moiety 'C3 N6 O6 D6' _chemical_formula_structural 'C3 N6 O6 D6' _chemical_formula_analytical 'C3 N6 O6 D6' _chemical_melting_point 478.5 _chemical_compound_source ? # for minerals and # natural products _symmetry_space_group_name_Hall 'P 2c -2ac' _exptl_crystal_F_000 912 _exptl_crystal_density_diffrn 2.282 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _cell_measurement_temperature 293 _cell_measurement_pressure 4780000 _cell_special_details ; ? ; _geom_special_details ? # The following item identifies the program(s) used (if appropriate). _computing_structure_solution 'FOX (FAVRE-NICOLIN)' #============================================================================== # 8. Phase information from GSAS _pd_phase_name PHASE_GAMMA_publish.cif _cell_length_a 12.6319(15) _cell_length_b 9.5554(14) _cell_length_c 11.0036(22) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1328.17(23) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 -x+1/2,+y,+z+1/2 3 +x+1/2,-y,+z 4 -x,-y,+z+1/2 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity C C1 0.1181(29) 1.082(4) 0.783(4) 1.0 Uiso 0.024(8) 4 C C2 0.0536(23) 0.886(5) 0.8968(25) 1.0 Uiso 0.024(8) 4 C C3 0.2162(15) 0.859(4) 0.7751(26) 1.0 Uiso 0.024(8) 4 N N10 0.1811(27) 0.985(4) 0.7116(30) 1.0 Uiso 0.0163(28) 4 N N11 0.0274(21) 1.013(4) 0.8294(30) 1.0 Uiso 0.0163(28) 4 N N12 0.1251(20) 0.792(4) 0.8293(30) 1.0 Uiso 0.0163(28) 4 N N13 0.200(5) 0.989(6) 0.5925(30) 1.0 Uiso 0.0163(28) 4 N N14 -0.0640(28) 1.001(5) 0.765(4) 1.0 Uiso 0.0163(28) 4 N N15 0.072(4) 0.703(4) 0.752(5) 1.0 Uiso 0.0163(28) 4 O O16 0.164(5) 1.095(6) 0.547(10) 1.0 Uiso 0.022(8) 4 O O17 0.254(5) 0.902(7) 0.540(9) 1.0 Uiso 0.022(8) 4 O O18 -0.064(7) 1.095(6) 0.690(7) 1.0 Uiso 0.022(8) 4 O O19 -0.138(5) 0.920(8) 0.774(7) 1.0 Uiso 0.022(8) 4 O O20 -0.013(5) 0.653(9) 0.784(7) 1.0 Uiso 0.022(8) 4 O O21 0.124(6) 0.644(7) 0.676(7) 1.0 Uiso 0.022(8) 4 C C4 0.6549(18) 0.4230(20) 0.0614(24) 1.0 Uiso 0.024(8) 4 C C5 0.5533(20) 0.5481(27) -0.0874(15) 1.0 Uiso 0.024(8) 4 C C6 0.6628(12) 0.6844(20) 0.0571(27) 1.0 Uiso 0.024(8) 4 N N16 0.6762(12) 0.5532(21) 0.1232(21) 1.0 Uiso 0.0163(28) 4 N N17 0.5590(16) 0.4306(21) -0.0040(17) 1.0 Uiso 0.0163(28) 4 N N18 0.5733(14) 0.6777(22) -0.0229(20) 1.0 Uiso 0.0163(28) 4 N N19 0.7132(11) 0.5519(31) 0.2388(23) 1.0 Uiso 0.0163(28) 4 N N20 0.4665(19) 0.4102(23) 0.0637(31) 1.0 Uiso 0.0163(28) 4 N N21 0.4954(15) 0.7720(24) -0.0081(24) 1.0 Uiso 0.0163(28) 4 O O22 0.728(6) 0.665(4) 0.290(4) 1.0 Uiso 0.022(8) 4 O O23 0.729(5) 0.439(4) 0.2845(33) 1.0 Uiso 0.022(8) 4 O O24 0.3848(18) 0.408(5) 0.005(5) 1.0 Uiso 0.022(8) 4 O O25 0.4755(30) 0.385(6) 0.1708(33) 1.0 Uiso 0.022(8) 4 O O26 0.4108(23) 0.750(4) -0.058(5) 1.0 Uiso 0.022(8) 4 O O27 0.5084(30) 0.871(5) 0.060(5) 1.0 Uiso 0.022(8) 4 D D11 0.154(7) 1.112(7) 0.869(5) 1.0 Uiso 0.045(6) 4 D D12 0.094(4) 1.175(6) 0.733(6) 1.0 Uiso 0.045(6) 4 D D21 0.096(5) 0.911(8) 0.9799(18) 1.0 Uiso 0.045(6) 4 D D22 -0.0190(28) 0.830(5) 0.919(5) 1.0 Uiso 0.045(6) 4 D D31 0.273(6) 0.875(9) 0.848(6) 1.0 Uiso 0.045(6) 4 D D32 0.2530(21) 0.788(4) 0.7104(35) 1.0 Uiso 0.045(6) 4 D D41 0.7195(18) 0.400(4) -0.001(4) 1.0 Uiso 0.045(6) 4 D D42 0.651(5) 0.343(6) 0.132(6) 1.0 Uiso 0.045(6) 4 D D51 0.6120(29) 0.5349(34) -0.1591(16) 1.0 Uiso 0.045(6) 4 D D52 0.4755(25) 0.564(8) -0.1280(22) 1.0 Uiso 0.045(6) 4 D D61 0.7329(14) 0.7044(29) 0.002(4) 1.0 Uiso 0.045(6) 4 D D62 0.6519(20) 0.7697(21) 0.122(4) 1.0 Uiso 0.045(6) 4 loop_ _atom_type_symbol _atom_type_number_in_cell C_ 24.0 N_ 48.0 O_ 48.0 D_ 48.0 # If you change Z, be sure to change all 3 of the following _chemical_formula_sum 'C3 N6 O6 D6' _chemical_formula_weight 228.071 _cell_formula_units_Z 8 # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N10 1.446(5) . 1_555 N C1 N11 1.416(5) . 1_555 N C1 D11 1.090(5) . 1_555 N C1 D12 1.090(5) . 1_555 N C2 N11 1.462(5) . 1_555 N C2 N12 1.472(5) . 1_555 N C2 D21 1.090(5) . 1_555 N C2 D22 1.090(5) . 1_555 N C3 N10 1.464(5) . 1_555 N C3 N12 1.444(5) . 1_555 N C3 D31 1.090(5) . 1_555 N C3 D32 1.090(5) . 1_555 N N10 C1 1.446(5) . 1_555 N N10 C3 1.464(5) . 1_555 N N10 N13 1.333(5) . 1_555 N N10 O16 2.11(10) . 1_555 N N11 C1 1.416(5) . 1_555 N N11 C2 1.462(5) . 1_555 N N11 N14 1.363(5) . 1_555 N N11 O18 2.07(8) . 1_555 N N11 D11 1.90(7) . 1_555 N N11 D12 2.055(6) . 1_555 N N12 C2 1.472(5) . 1_555 N N12 C3 1.444(5) . 1_555 N N12 N15 1.387(5) . 1_555 N N12 D21 2.04(6) . 1_555 N N12 D31 2.05(7) . 1_555 N N13 N10 1.333(5) . 1_555 N N13 O16 1.223(5) . 1_555 N N13 O17 1.216(5) . 1_555 N N14 N11 1.363(5) . 1_555 N N14 O18 1.219(5) . 1_555 N N14 O19 1.216(5) . 1_555 N N15 N12 1.387(5) . 1_555 N N15 O20 1.222(5) . 1_555 N N15 O21 1.207(5) . 1_555 N O16 N10 2.11(10) . 1_555 N O16 N13 1.223(5) . 1_555 N O16 O17 2.17(6) . 1_555 N O17 N13 1.216(5) . 1_555 N O17 O16 2.17(6) . 1_555 N O17 D21 2.01(11) . 2_554 N O18 N11 2.07(8) . 1_555 N O18 N14 1.219(5) . 1_555 N O18 O19 2.13(6) . 1_555 N O19 N14 1.216(5) . 1_555 N O19 O18 2.13(6) . 1_555 N O20 N15 1.222(5) . 1_555 N O20 O21 2.11(6) . 1_555 N O21 N15 1.207(5) . 1_555 N O21 O20 2.11(6) . 1_555 N C4 N16 1.443(5) . 1_555 N C4 N17 1.410(5) . 1_555 N C4 D41 1.089(5) . 1_555 N C4 D42 1.091(5) . 1_555 N C5 N17 1.452(5) . 1_555 N C5 N18 1.450(5) . 1_555 N C5 D51 1.090(5) . 1_555 N C5 D52 1.090(5) . 1_555 N C6 N16 1.460(5) . 1_555 N C6 N18 1.434(5) . 1_555 N C6 D61 1.089(5) . 1_555 N C6 D62 1.090(5) . 1_555 N N16 C4 1.443(5) . 1_555 N N16 C6 1.460(5) . 1_555 N N16 N19 1.355(5) . 1_555 N N16 D42 2.04(6) . 1_555 N N17 C4 1.410(5) . 1_555 N N17 C5 1.452(5) . 1_555 N N17 N20 1.400(5) . 1_555 N N17 D41 2.049(6) . 1_555 N N18 C5 1.450(5) . 1_555 N N18 C6 1.434(5) . 1_555 N N18 N21 1.345(5) . 1_555 N N18 D52 2.01(5) . 1_555 N N18 D61 2.050(5) . 1_555 N N19 N16 1.355(5) . 1_555 N N19 O22 1.236(5) . 1_555 N N19 O23 1.210(5) . 1_555 N N20 N17 1.400(5) . 1_555 N N20 O24 1.215(5) . 1_555 N N20 O25 1.208(5) . 1_555 N N21 N18 1.345(5) . 1_555 N N21 O26 1.221(5) . 1_555 N N21 O27 1.218(5) . 1_555 N O22 N19 1.236(5) . 1_555 N O22 O23 2.167(6) . 1_555 N O23 N19 1.210(5) . 1_555 N O23 O22 2.167(6) . 1_555 N O24 N20 1.215(5) . 1_555 N O24 O25 2.160(6) . 1_555 N O25 N20 1.208(5) . 1_555 N O25 O24 2.160(6) . 1_555 N O26 N21 1.221(5) . 1_555 N O26 O27 2.132(6) . 1_555 N O27 N21 1.218(5) . 1_555 N O27 O26 2.132(6) . 1_555 N D11 C1 1.090(5) . 1_555 N D11 N11 1.90(7) . 1_555 N D11 D12 1.780(6) . 1_555 N D12 C1 1.090(5) . 1_555 N D12 N11 2.055(6) . 1_555 N D12 D11 1.780(6) . 1_555 N D21 C2 1.090(5) . 1_555 N D21 N12 2.04(6) . 1_555 N D21 O17 2.01(11) . 2_555 N D21 D22 1.781(6) . 1_555 N D22 C2 1.090(5) . 1_555 N D22 D21 1.781(6) . 1_555 N D31 C3 1.090(5) . 1_555 N D31 N12 2.05(7) . 1_555 N D31 D32 1.75(7) . 1_555 N D32 C3 1.090(5) . 1_555 N D32 D31 1.75(7) . 1_555 N D32 D42 1.94(5) . 4_665 N D41 C4 1.089(5) . 1_555 N D41 N17 2.049(6) . 1_555 N D41 D42 1.780(6) . 1_555 N D42 C4 1.091(5) . 1_555 N D42 N16 2.04(6) . 1_555 N D42 D32 1.94(5) . 4_664 N D42 D41 1.780(6) . 1_555 N D51 C5 1.090(5) . 1_555 N D51 D52 1.780(6) . 1_555 N D52 C5 1.090(5) . 1_555 N D52 N18 2.01(5) . 1_555 N D52 D51 1.780(6) . 1_555 N D61 C6 1.089(5) . 1_555 N D61 N18 2.050(5) . 1_555 N D61 D62 1.779(6) . 1_555 N D62 C6 1.090(5) . 1_555 N D62 D61 1.779(6) . 1_555 N loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N10 C1 N11 110.291(34) 1_555 . 1_555 N N10 C1 D11 114(5) 1_555 . 1_555 N N10 C1 D12 114(4) 1_555 . 1_555 N N11 C1 D11 98(5) 1_555 . 1_555 N N11 C1 D12 109.51(5) 1_555 . 1_555 N D11 C1 D12 109.49(6) 1_555 . 1_555 N N11 C2 N12 112.800(24) 1_555 . 1_555 N N11 C2 D21 111(5) 1_555 . 1_555 N N11 C2 D22 109.51(4) 1_555 . 1_555 N N12 C2 D21 105(5) 1_555 . 1_555 N N12 C2 D22 109.50(4) 1_555 . 1_555 N D21 C2 D22 109.50(5) 1_555 . 1_555 N N10 C3 N12 108.624(28) 1_555 . 1_555 N N10 C3 D31 116(7) 1_555 . 1_555 N N10 C3 D32 109.49(4) 1_555 . 1_555 N N12 C3 D31 107(6) 1_555 . 1_555 N N12 C3 D32 109.50(4) 1_555 . 1_555 N D31 C3 D32 107(6) 1_555 . 1_555 N C1 N10 C3 115.659(23) 1_555 . 1_555 N C1 N10 N13 128(4) 1_555 . 1_555 N C3 N10 N13 116(4) 1_555 . 1_555 N C1 N11 C2 112.700(28) 1_555 . 1_555 N C1 N11 N14 122.4(29) 1_555 . 1_555 N C2 N11 N14 112.6(30) 1_555 . 1_555 N C2 N12 C3 115.419(25) 1_555 . 1_555 N C2 N12 N15 112.8(25) 1_555 . 1_555 N C3 N12 N15 113.9(30) 1_555 . 1_555 N N10 N13 O16 111(8) 1_555 . 1_555 N N10 N13 O17 123(8) 1_555 . 1_555 N O16 N13 O17 126(6) 1_555 . 1_555 N N11 N14 O18 107(6) 1_555 . 1_555 N N11 N14 O19 131(5) 1_555 . 1_555 N O18 N14 O19 122(6) 1_555 . 1_555 N N12 N15 O20 119(5) 1_555 . 1_555 N N12 N15 O21 117(6) 1_555 . 1_555 N O20 N15 O21 120(6) 1_555 . 1_555 N N16 C4 N17 110.9(7) 1_555 . 1_555 N N16 C4 D41 109.501(31) 1_555 . 1_555 N N16 C4 D42 106(5) 1_555 . 1_555 N N17 C4 D41 109.50(4) 1_555 . 1_555 N N17 C4 D42 111(4) 1_555 . 1_555 N D41 C4 D42 109.51(4) 1_555 . 1_555 N N17 C5 N18 110.011(26) 1_555 . 1_555 N N17 C5 D51 109.501(28) 1_555 . 1_555 N N17 C5 D52 114(4) 1_555 . 1_555 N N18 C5 D51 109.501(28) 1_555 . 1_555 N N18 C5 D52 104(4) 1_555 . 1_555 N D51 C5 D52 109.50(5) 1_555 . 1_555 N N16 C6 N18 111.019(17) 1_555 . 1_555 N N16 C6 D61 109.502(34) 1_555 . 1_555 N N16 C6 D62 109.41(4) 1_555 . 1_555 N N18 C6 D61 107.89(8) 1_555 . 1_555 N N18 C6 D62 109.498(34) 1_555 . 1_555 N D61 C6 D62 109.50(4) 1_555 . 1_555 N C4 N16 C6 118.943(25) 1_555 . 1_555 N C4 N16 N19 119.925(28) 1_555 . 1_555 N C6 N16 N19 121.044(28) 1_555 . 1_555 N C4 N17 C5 113.912(16) 1_555 . 1_555 N C4 N17 N20 115.941(34) 1_555 . 1_555 N C5 N17 N20 113.731(27) 1_555 . 1_555 N C5 N18 C6 118.470(18) 1_555 . 1_555 N C5 N18 N21 120.260(31) 1_555 . 1_555 N C6 N18 N21 118.209(27) 1_555 . 1_555 N N16 N19 O22 118.259(28) 1_555 . 1_555 N N16 N19 O23 117.019(26) 1_555 . 1_555 N O22 N19 O23 124.72(4) 1_555 . 1_555 N N17 N20 O24 115.55(4) 1_555 . 1_555 N N17 N20 O25 118.007(33) 1_555 . 1_555 N O24 N20 O25 126.09(4) 1_555 . 1_555 N N18 N21 O26 118.191(29) 1_555 . 1_555 N N18 N21 O27 119.762(32) 1_555 . 1_555 N O26 N21 O27 121.892(34) 1_555 . 1_555 N _pd_meas_number_of_points 2528 _pd_proc_number_of_points 2528 _reflns_number_total 761 _reflns_limit_h_min 0 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _reflns_d_resolution_high 0.998 _reflns_d_resolution_low 4.149 #--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--# # Attachment 'gamma-RDX.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 663455' _audit_creation_date 07-07-19 _audit_creation_method CRYSTALS_ver_12.80 _oxford_structure_analysis_title CRYSTALS_cif _chemical_name_systematic cyclotrimethylene-trinitramine _chemical_melting_point 478.5 _cell_length_a 12.5650(19) _cell_length_b 9.4769(6) _cell_length_c 10.9297(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1301.5(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 = 2.27 Fooo = 912.00 Mu = 2.16 M = 444.23 # Found Formula = C3 H6 N6 O6 # Dc = 2.27 FOOO = 912.00 Mu = 2.16 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 1200 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 2.267 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.216 # Sheldrick geometric approximatio 0.97 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker Nonius Apex II CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.67100 _diffrn_measurement_method \w _computing_data_collection 'Smart Apex II (Bruker Nonius)' _computing_data_reduction Saint _computing_cell_refinement Saint _computing_structure_solution 'FOX (FAVRE-NICOLIN)' _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 293 _diffrn_ambient_pressure 5200000 _diffrn_reflns_number 4339 _reflns_number_total 872 _diffrn_reflns_av_R_equivalents 0.079 # Number of reflections with Friedels Law is 872 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1341 _diffrn_reflns_theta_min 2.541 _diffrn_reflns_theta_max 24.865 _diffrn_measured_fraction_theta_max 0.617 _diffrn_reflns_theta_full 18.648 _diffrn_measured_fraction_theta_full 0.729 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min 0 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _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 -0.55 _refine_diff_density_max 0.94 _refine_ls_number_reflns 872 _refine_ls_number_restraints 1 _refine_ls_number_parameters 123 #_refine_ls_R_factor_ref 0.0893 _refine_ls_wR_factor_ref 0.1809 _refine_ls_goodness_of_fit_ref 0.8652 #_reflns_number_all 872 _refine_ls_R_factor_all 0.0893 _refine_ls_wR_factor_all 0.1809 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 655 _refine_ls_R_factor_gt 0.0717 _refine_ls_wR_factor_gt 0.1723 _refine_ls_shift/su_max 0.000056 _refine_ls_abs_structure_Flack 10(14) _refine_ls_abs_structure_details 'Flack, 0 Friedel-pairs' # 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 ad _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 ; w=1/[\s^2^(F^2^) + 0.00 + 3.90P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.1232(11) 1.0792(11) 0.7875(11) 0.025(3) 1.0000 Uiso . . . . . . C2 C 0.0539(11) 0.8773(11) 0.8964(11) 0.021(2) 1.0000 Uiso . . . . . . C3 C 0.2156(10) 0.8541(10) 0.7729(12) 0.023(2) 1.0000 Uiso . . . . . . N10 N 0.1845(9) 0.9843(9) 0.7141(9) 0.020(2) 1.0000 Uiso . . . . . . N11 N 0.0289(10) 1.0080(10) 0.8352(8) 0.021(2) 1.0000 Uiso . . . . . . N12 N 0.1209(9) 0.7872(9) 0.8234(8) 0.020(2) 1.0000 Uiso . . . . . . N13 N 0.1955(11) 1.0052(11) 0.5942(9) 0.033(3) 1.0000 Uiso . . . . . . N14 N -0.0590(8) 1.0080(9) 0.7608(8) 0.017(2) 1.0000 Uiso . . . . . . N15 N 0.0727(9) 0.6949(9) 0.7440(9) 0.022(2) 1.0000 Uiso . . . . . . O16 O 0.1563(10) 1.1114(9) 0.5501(10) 0.046(2) 1.0000 Uiso . . . . . . O17 O 0.2465(10) 0.9184(9) 0.5388(10) 0.052(3) 1.0000 Uiso . . . . . . O18 O -0.0665(9) 1.1038(8) 0.6866(8) 0.031(2) 1.0000 Uiso . . . . . . O19 O -0.1275(8) 0.9235(8) 0.7822(8) 0.033(2) 1.0000 Uiso . . . . . . O20 O -0.0192(8) 0.6659(8) 0.7668(8) 0.0279(19) 1.0000 Uiso . . . . . . O21 O 0.1239(8) 0.6448(7) 0.6621(8) 0.0272(19) 1.0000 Uiso . . . . . . C4 C 0.6574(12) 0.4212(11) 0.0638(12) 0.025(3) 1.0000 Uiso . . . . . . C5 C 0.5519(10) 0.5461(10) -0.0884(11) 0.020(2) 1.0000 Uiso . . . . . . C6 C 0.6633(10) 0.6855(10) 0.0522(12) 0.021(2) 1.0000 Uiso . . . . . . N16 N 0.6770(8) 0.5555(9) 0.1229(8) 0.017(2) 1.0000 Uiso . . . . . . N17 N 0.5586(8) 0.4274(8) -0.0042(8) 0.016(2) 1.0000 Uiso . . . . . . N18 N 0.5726(8) 0.6774(9) -0.0235(8) 0.018(2) 1.0000 Uiso . . . . . . N19 N 0.7114(9) 0.5619(8) 0.2385(8) 0.018(2) 1.0000 Uiso . . . . . . N20 N 0.4652(8) 0.4052(8) 0.0640(7) 0.0151(19) 1.0000 Uiso . . . . . . N21 N 0.4925(8) 0.7670(8) -0.0082(7) 0.018(2) 1.0000 Uiso . . . . . . O22 O 0.7427(8) 0.6755(7) 0.2775(8) 0.0248(17) 1.0000 Uiso . . . . . . O23 O 0.7088(8) 0.4521(7) 0.2981(8) 0.0228(18) 1.0000 Uiso . . . . . . O24 O 0.3830(9) 0.4201(8) 0.0086(8) 0.034(2) 1.0000 Uiso . . . . . . O25 O 0.4741(8) 0.3616(8) 0.1673(8) 0.032(2) 1.0000 Uiso . . . . . . O26 O 0.4117(8) 0.7519(8) -0.0731(8) 0.0259(19) 1.0000 Uiso . . . . . . O27 O 0.5022(7) 0.8669(7) 0.0630(8) 0.0197(17) 1.0000 Uiso . . . . . . H11 H 0.1671 1.1095 0.8560 0.0360 1.0000 Uiso R . . . . . H12 H 0.1029 1.1609 0.7398 0.0363 1.0000 Uiso R . . . . . H21 H 0.0898 0.8979 0.9731 0.0301 1.0000 Uiso R . . . . . H22 H -0.0116 0.8298 0.9126 0.0299 1.0000 Uiso R . . . . . H31 H 0.2669 0.8716 0.8383 0.0340 1.0000 Uiso R . . . . . H32 H 0.2473 0.7911 0.7135 0.0339 1.0000 Uiso R . . . . . H41 H 0.7156 0.3998 0.0084 0.0360 1.0000 Uiso R . . . . . H42 H 0.6526 0.3484 0.1254 0.0359 1.0000 Uiso R . . . . . H51 H 0.6044 0.5342 -0.1526 0.0268 1.0000 Uiso R . . . . . H52 H 0.4806 0.5481 -0.1221 0.0268 1.0000 Uiso R . . . . . H61 H 0.7259 0.6986 0.0011 0.0303 1.0000 Uiso R . . . . . H62 H 0.6552 0.7662 0.1074 0.0300 1.0000 Uiso R . . . . . _refine_ls_extinction_coef 400(100) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _oxford_refine_ls_scale 0.991(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 . N10 . 1.430(15) yes C1 . N11 . 1.460(18) yes C1 . H11 . 0.973 no C1 . H12 . 0.968 no C2 . N11 . 1.442(14) yes C2 . N12 . 1.440(15) yes C2 . H21 . 0.972 no C2 . H22 . 0.955 no C3 . N10 . 1.446(14) yes C3 . N12 . 1.457(15) yes C3 . H31 . 0.976 no C3 . H32 . 0.968 no N10 . N13 . 1.332(14) yes N11 . N14 . 1.372(14) yes N12 . N15 . 1.373(14) yes N13 . O16 . 1.220(14) yes N13 . O17 . 1.207(15) yes N14 . O18 . 1.222(12) yes N14 . O19 . 1.198(12) yes N15 . O20 . 1.213(13) yes N15 . O21 . 1.201(13) yes C4 . N16 . 1.448(14) yes C4 . N17 . 1.449(17) yes C4 . H41 . 0.971 no C4 . H42 . 0.966 no C5 . N17 . 1.455(13) yes C5 . N18 . 1.456(13) yes C5 . H51 . 0.969 no C5 . H52 . 0.969 no C6 . N16 . 1.464(14) yes C6 . N18 . 1.411(16) yes C6 . H61 . 0.972 no C6 . H62 . 0.979 no N16 . N19 . 1.337(12) yes N17 . N20 . 1.407(13) yes N18 . N21 . 1.327(13) yes N19 . O22 . 1.223(11) yes N19 . O23 . 1.227(10) yes N20 . O24 . 1.205(13) yes N20 . O25 . 1.207(12) yes N21 . O26 . 1.246(14) yes N21 . O27 . 1.231(11) 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 . 110.3(8) yes N10 . C1 . H11 . 108.2 no N11 . C1 . H11 . 108.8 no N10 . C1 . H12 . 110.0 no N11 . C1 . H12 . 110.4 no H11 . C1 . H12 . 109.2 no N11 . C2 . N12 . 112.2(10) yes N11 . C2 . H21 . 109.2 no N12 . C2 . H21 . 109.0 no N11 . C2 . H22 . 107.7 no N12 . C2 . H22 . 109.1 no H21 . C2 . H22 . 109.6 no N10 . C3 . N12 . 108.6(9) yes N10 . C3 . H31 . 111.0 no N12 . C3 . H31 . 109.6 no N10 . C3 . H32 . 109.8 no N12 . C3 . H32 . 108.8 no H31 . C3 . H32 . 108.9 no C3 . N10 . C1 . 115.6(9) yes C3 . N10 . N13 . 122.4(9) yes C1 . N10 . N13 . 120.9(10) yes C1 . N11 . C2 . 112.7(11) yes C1 . N11 . N14 . 116.2(8) yes C2 . N11 . N14 . 116.8(9) yes C3 . N12 . C2 . 115.4(8) yes C3 . N12 . N15 . 113.5(9) yes C2 . N12 . N15 . 118.1(11) yes N10 . N13 . O16 . 118.0(11) yes N10 . N13 . O17 . 116.6(11) yes O16 . N13 . O17 . 125.4(12) yes N11 . N14 . O18 . 117.1(9) yes N11 . N14 . O19 . 117.5(9) yes O18 . N14 . O19 . 124.9(10) yes N12 . N15 . O20 . 115.7(10) yes N12 . N15 . O21 . 119.2(11) yes O20 . N15 . O21 . 125.0(10) yes N16 . C4 . N17 . 109.8(9) yes N16 . C4 . H41 . 109.6 no N17 . C4 . H41 . 109.5 no N16 . C4 . H42 . 109.1 no N17 . C4 . H42 . 109.4 no H41 . C4 . H42 . 109.5 no N17 . C5 . N18 . 110.0(9) yes N17 . C5 . H51 . 109.2 no N18 . C5 . H51 . 109.3 no N17 . C5 . H52 . 108.0 no N18 . C5 . H52 . 109.4 no H51 . C5 . H52 . 110.8 no N16 . C6 . N18 . 111.0(9) yes N16 . C6 . H61 . 108.4 no N18 . C6 . H61 . 108.9 no N16 . C6 . H62 . 110.1 no N18 . C6 . H62 . 108.6 no H61 . C6 . H62 . 109.8 no C6 . N16 . C4 . 119.0(9) yes C6 . N16 . N19 . 119.9(9) yes C4 . N16 . N19 . 121.0(9) yes C5 . N17 . C4 . 113.9(9) yes C5 . N17 . N20 . 113.7(9) yes C4 . N17 . N20 . 115.9(9) yes C5 . N18 . C6 . 118.4(9) yes C5 . N18 . N21 . 118.2(10) yes C6 . N18 . N21 . 120.3(9) yes N16 . N19 . O22 . 118.2(8) yes N16 . N19 . O23 . 117.1(8) yes O22 . N19 . O23 . 124.7(9) yes N17 . N20 . O24 . 115.5(9) yes N17 . N20 . O25 . 118.0(9) yes O24 . N20 . O25 . 126.2(10) yes N18 . N21 . O26 . 118.2(9) yes N18 . N21 . O27 . 119.7(9) yes O26 . N21 . O27 . 121.9(9) 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 N11 . H21 . O17 2_555 124.4 1.987 2.186 3.693 yes N17 . H52 . O26 . 123.2 1.983 2.183 3.665 yes