#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:05:02 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247595 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125623.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7125623 loop_ _publ_author_name 'Liu, Tianlin' 'Liao, Sicheng' 'Song, Siwei' 'Wang, Kangcai' 'Jin, Yunhe' 'Zhang, Qinghua' _publ_section_title ; Combination of gem-dinitromethyl functionality and a 5-amino-1,3,4-oxadiazole framework for zwitterionic energetic materials. ; _journal_issue 2 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 209 _journal_page_last 212 _journal_paper_doi 10.1039/c9cc08182h _journal_volume 56 _journal_year 2019 _chemical_formula_moiety 'C3 H3 N5 O5' _chemical_formula_sum 'C3 H3 N5 O5' _chemical_formula_weight 189.10 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2017-03-30 _audit_creation_method ; Olex2 1.2-beta (compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328) ; _audit_update_record ; 2019-06-27 deposited with the CCDC. 2019-11-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2688(10) _cell_length_b 6.1121(7) _cell_length_c 13.2779(17) _cell_measurement_reflns_used 2027 _cell_measurement_temperature 173 _cell_measurement_theta_max 27.06 _cell_measurement_theta_min 3.07 _cell_volume 671.06(14) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SIR2004 (Burla et al., 2007)' _diffrn_ambient_temperature 173 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0323 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3692 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.492 _diffrn_reflns_theta_min 3.068 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6640 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0846 before and 0.0410 after correction. The Ratio of minimum to maximum transmission is 0.8906. The \l/2 correction factor is 0.0015.' _exptl_crystal_colour 'clear yellowish yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.200 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.051 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.1(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 123 _refine_ls_number_reflns 1436 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0292 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.0299P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.0779 _reflns_Friedel_coverage 0.919 _reflns_Friedel_fraction_full 0.995 _reflns_Friedel_fraction_max 0.992 _reflns_number_gt 1367 _reflns_number_total 1436 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; mo_ltl-4-2-2_0ma.res created by SHELXL-2014/7 TITL mo_LTL-4-2-2_0ma in Pca2(1) CELL 0.71073 8.2688 6.1121 13.2779 90 90 90 ZERR 4 0.001 0.0007 0.0017 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,+Y,0.5+Z SYMM 0.5+X,-Y,+Z SFAC C H N O UNIT 12 12 20 20 L.S. 20 PLAN -2 0 0 TEMP -100.15 HTAB BOND $H CONF fmap 2 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 REM REM REM WGHT 0.047500 0.029900 BASF 0.10811 FVAR 0.37566 O5 4 -0.246228 0.107425 -0.309301 11.00000 0.02291 0.02129 = 0.01756 -0.00470 0.00266 -0.00313 O3 4 -0.347251 -0.274475 -0.577661 11.00000 0.03269 0.02914 = 0.01674 -0.00609 -0.00106 0.00599 N4 3 -0.388049 0.016969 -0.179886 11.00000 0.02496 0.02354 = 0.01568 -0.00288 0.00395 0.00192 O4 4 -0.470097 -0.023859 -0.490160 11.00000 0.03055 0.02846 = 0.02276 -0.00447 -0.00648 0.01216 O2 4 -0.073849 -0.377102 -0.329793 11.00000 0.02514 0.03212 = 0.02271 0.00244 -0.00539 0.00459 N1 3 -0.366665 -0.177211 -0.497481 11.00000 0.01962 0.01779 = 0.01616 -0.00147 0.00001 -0.00067 N3 3 -0.400301 -0.157358 -0.245634 11.00000 0.02284 0.02286 = 0.01725 -0.00286 0.00046 0.00045 O1 4 -0.117134 -0.485214 -0.482661 11.00000 0.04314 0.04591 = 0.03216 -0.01691 -0.00748 0.02456 N5 3 -0.251224 0.358280 -0.180849 11.00000 0.04113 0.02464 = 0.02365 -0.00904 0.00451 -0.00611 AFIX 93 H5A 2 -0.282992 0.396438 -0.120083 11.00000 -1.20000 H5B 2 -0.188872 0.446367 -0.216070 11.00000 -1.20000 AFIX 0 C3 1 -0.296275 0.172316 -0.218478 11.00000 0.02145 0.02400 = 0.01644 -0.00227 -0.00161 0.00413 C2 1 -0.315209 -0.099212 -0.321617 11.00000 0.01599 0.01867 = 0.01832 -0.00171 -0.00146 0.00064 C1 1 -0.280620 -0.222162 -0.411816 11.00000 0.01971 0.02101 = 0.01680 -0.00273 -0.00076 0.00020 N2 3 -0.152726 -0.369930 -0.410360 11.00000 0.02292 0.02153 = 0.02065 -0.00185 -0.00124 0.00293 H4 2 -0.429356 0.021532 -0.126573 11.00000 0.04402 HKLF 4 REM mo_LTL-4-2-2_0ma in Pca2(1) REM R1 = 0.0292 for 1367 Fo > 4sig(Fo) and 0.0309 for all 1436 data REM 123 parameters refined using 1 restraints END WGHT 0.0475 0.0299 REM Instructions for potential hydrogen bonds EQIV $1 -x-1/2, y+1, z+1/2 HTAB N5 O1_$1 EQIV $2 x, y+1, z HTAB N5 O2_$2 EQIV $3 -x-1, -y, z+1/2 HTAB N4 O3_$3 HTAB N4 O4_$3 HTAB N4 N1_$3 REM Highest difference peak 0.200, deepest hole -0.183, 1-sigma level 0.051 Q1 1 -0.2867 -0.1675 -0.3624 11.00000 0.05 0.20 Q2 1 0.1426 0.6104 0.4589 11.00000 0.05 0.16 REM The information below was added by Olex2. REM REM R1 = 0.0292 for 1367 Fo > 4sig(Fo) and 0.0309 for all 4111 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.20, deepest hole -0.18 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0309 REM R1_gt = 0.0292 REM wR_ref = 0.0779 REM GOOF = 1.105 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 4111 REM Reflections_gt = 1367 REM Parameters = n/a REM Hole = -0.18 REM Peak = 0.20 REM Flack = n/a ; _cod_data_source_file c9cc08182h2.cif _cod_data_source_block mo_ltl-4-2-2_0ma _cod_depositor_comments 'Adding full bibliography for 7125621--7125624.cif.' _cod_database_code 7125623 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.9(17) 0.1(17) 2. Fixed Uiso At 1.2 times of: All N(H,H) groups 3.a X=CH2 refined with riding coordinates: N5(H5A,H5B) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' 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_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O5 O -0.2462(2) 0.1074(3) -0.30930(13) 0.0206(4) Uani 1 1 d . O3 O -0.3473(2) -0.2745(3) -0.57766(12) 0.0262(4) Uani 1 1 d . N4 N -0.3880(2) 0.0170(3) -0.17989(15) 0.0214(4) Uani 1 1 d . O4 O -0.4701(2) -0.0239(3) -0.49016(13) 0.0273(4) Uani 1 1 d . O2 O -0.0738(2) -0.3771(3) -0.32979(12) 0.0267(4) Uani 1 1 d . N1 N -0.3667(2) -0.1772(3) -0.49748(13) 0.0179(4) Uani 1 1 d . N3 N -0.4003(3) -0.1574(3) -0.24563(14) 0.0210(4) Uani 1 1 d . O1 O -0.1171(2) -0.4852(4) -0.48266(14) 0.0404(6) Uani 1 1 d . N5 N -0.2512(3) 0.3583(3) -0.18085(17) 0.0298(5) Uani 1 1 d . H5A H -0.2830 0.3964 -0.1201 0.036 Uiso 1 1 calc R H5B H -0.1889 0.4464 -0.2161 0.036 Uiso 1 1 calc R C3 C -0.2963(3) 0.1723(4) -0.21848(17) 0.0206(5) Uani 1 1 d . C2 C -0.3152(3) -0.0992(4) -0.32162(17) 0.0177(4) Uani 1 1 d . C1 C -0.2806(3) -0.2222(4) -0.41182(16) 0.0192(5) Uani 1 1 d . N2 N -0.1527(3) -0.3699(3) -0.41036(15) 0.0217(4) Uani 1 1 d . H4 H -0.429(5) 0.022(6) -0.127(3) 0.044(10) Uiso 1 1 d . 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 O5 0.0229(8) 0.0213(9) 0.0176(7) -0.0047(6) 0.0027(6) -0.0031(7) O3 0.0327(9) 0.0291(10) 0.0167(7) -0.0061(7) -0.0011(7) 0.0060(8) N4 0.0250(11) 0.0235(11) 0.0157(9) -0.0029(7) 0.0040(7) 0.0019(8) O4 0.0306(10) 0.0285(10) 0.0228(7) -0.0045(7) -0.0065(7) 0.0122(8) O2 0.0251(9) 0.0321(11) 0.0227(9) 0.0024(7) -0.0054(7) 0.0046(7) N1 0.0196(10) 0.0178(10) 0.0162(8) -0.0015(8) 0.0000(7) -0.0007(7) N3 0.0228(9) 0.0229(11) 0.0173(9) -0.0029(7) 0.0005(7) 0.0004(8) O1 0.0431(12) 0.0459(14) 0.0322(11) -0.0169(9) -0.0075(8) 0.0246(10) N5 0.0411(13) 0.0246(11) 0.0236(10) -0.0090(9) 0.0045(9) -0.0061(9) C3 0.0215(12) 0.0240(12) 0.0164(9) -0.0023(9) -0.0016(8) 0.0041(8) C2 0.0160(10) 0.0187(11) 0.0183(10) -0.0017(8) -0.0015(8) 0.0006(8) C1 0.0197(11) 0.0210(12) 0.0168(9) -0.0027(8) -0.0008(7) 0.0002(9) N2 0.0229(11) 0.0215(11) 0.0207(9) -0.0019(7) -0.0012(8) 0.0029(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C3 O5 C2 104.36(19) N3 N4 H4 124(3) C3 N4 N3 110.61(19) C3 N4 H4 125(3) O3 N1 O4 120.65(18) O3 N1 C1 123.65(19) O4 N1 C1 115.69(19) C2 N3 N4 104.1(2) H5A N5 H5B 120.0 C3 N5 H5A 120.0 C3 N5 H5B 120.0 N4 C3 O5 108.4(2) N5 C3 O5 121.3(2) N5 C3 N4 130.3(2) O5 C2 C1 119.19(19) N3 C2 O5 112.6(2) N3 C2 C1 128.2(2) N1 C1 C2 118.8(2) N1 C1 N2 122.5(2) N2 C1 C2 118.52(19) O2 N2 C1 115.48(19) O1 N2 O2 121.5(2) O1 N2 C1 123.0(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O5 C3 1.335(3) O5 C2 1.395(3) O3 N1 1.230(2) N4 N3 1.381(3) N4 C3 1.319(3) N4 H4 0.79(4) O4 N1 1.273(2) O2 N2 1.254(3) N1 C1 1.369(3) N3 C2 1.280(3) O1 N2 1.227(3) N5 H5A 0.8800 N5 H5B 0.8800 N5 C3 1.296(3) C2 C1 1.443(3) C1 N2 1.391(3) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion O5 C2 C1 N1 -82.0(3) O5 C2 C1 N2 93.2(3) O3 N1 C1 C2 -179.2(2) O3 N1 C1 N2 5.9(4) N4 N3 C2 O5 0.1(2) N4 N3 C2 C1 177.6(2) O4 N1 C1 C2 1.4(3) O4 N1 C1 N2 -173.6(2) N1 C1 N2 O2 172.5(2) N1 C1 N2 O1 -6.9(4) N3 N4 C3 O5 0.2(3) N3 N4 C3 N5 -178.1(3) N3 C2 C1 N1 100.6(3) N3 C2 C1 N2 -84.3(3) C3 O5 C2 N3 0.1(3) C3 O5 C2 C1 -177.8(2) C3 N4 N3 C2 -0.1(2) C2 O5 C3 N4 -0.1(2) C2 O5 C3 N5 178.3(2) C2 C1 N2 O2 -2.5(3) C2 C1 N2 O1 178.1(2) loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.9(17) 2 0.1(17)