#------------------------------------------------------------------------------ #$Date: 2021-11-03 03:34:01 +0200 (Wed, 03 Nov 2021) $ #$Revision: 270221 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061035.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_7061035 loop_ _publ_author_name 'Lang, Qing' 'wang, qian' 'Lin, Qiuhan' 'Xu, Yuangang' 'Lu, Ming' _publ_section_title ; C5H2N14O6: Achieving azido-based materials with zero oxygen balance and good energetic performance ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04188F _journal_year 2021 _chemical_formula_moiety 'C5 H2 N14 O6' _chemical_formula_sum 'C5 H2 N14 O6' _chemical_formula_weight 354.21 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-10-16 deposited with the CCDC. 2021-10-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.855(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.7238(9) _cell_length_b 6.6508(6) _cell_length_c 20.1429(18) _cell_measurement_reflns_used 1952 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.33 _cell_measurement_theta_min 3.23 _cell_volume 1301.0(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX3' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'PHOTON 100 CMOS detector' _diffrn_measurement_method 'omega scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 7444 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.020 _diffrn_reflns_theta_max 25.020 _diffrn_reflns_theta_min 3.226 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2014)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.808 _exptl_crystal_description needle _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.202 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 2273 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0480 _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^)+(0.0424P)^2^+0.7834P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0980 _refine_ls_wR_factor_ref 0.1121 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1531 _reflns_number_total 2273 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04188f2.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7061035 _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. ; _shelx_estimated_absorpt_t_min 0.961 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1 in P2(1)/n CELL 0.71073 9.7238 6.6508 20.1429 90.000 92.855 90.000 ZERR 4.00 0.0009 0.0006 0.0018 0.000 0.004 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 20 8 56 24 L.S. 10 size 0.25 0.09 0.05 BOND $h acta omit -2 50.05 FMAP 2 PLAN 20 TEMP -100.150 WGHT 0.042400 0.783400 FVAR 0.22266 MOLE 1 C1 1 0.765335 0.575308 0.153446 11.00000 0.02250 0.01996 = 0.03078 0.01015 0.00841 0.00254 AFIX 23 H1A 2 0.698604 0.474904 0.135065 11.00000 -1.20000 H1B 2 0.753380 0.585105 0.201861 11.00000 -1.20000 AFIX 0 C2 1 1.138223 0.421547 0.200694 11.00000 0.03269 0.03976 = 0.03396 0.00528 0.00387 0.00491 C3 1 0.991908 0.441616 0.195383 11.00000 0.03122 0.02455 = 0.03205 0.00269 0.00503 0.00147 C4 1 0.701683 0.885870 0.003700 11.00000 0.03389 0.01926 = 0.02271 -0.00361 -0.00178 0.01087 C5 1 0.659540 0.791840 0.062710 11.00000 0.02474 0.01733 = 0.02681 -0.00368 -0.00288 0.00628 N1 3 0.904653 0.505967 0.142426 11.00000 0.02430 0.02172 = 0.02300 0.00008 0.00528 0.00478 N2 3 0.918995 0.409963 0.081103 11.00000 0.03374 0.02325 = 0.03743 -0.00562 0.00955 0.00272 N3 3 1.176771 0.372199 0.261009 11.00000 0.03616 0.06848 = 0.03615 0.01324 0.00357 0.01013 N4 3 0.942728 0.403644 0.253208 11.00000 0.03328 0.05053 = 0.03640 0.01228 0.00532 0.00516 N5 3 1.226587 0.449141 0.149304 11.00000 0.02339 0.06675 = 0.03706 0.00832 0.00128 0.00140 N6 3 1.350264 0.414358 0.166828 11.00000 0.02827 0.05850 = 0.03478 -0.00512 0.00054 -0.00353 N7 3 1.463281 0.386590 0.174280 11.00000 0.02993 0.09115 = 0.04342 -0.00822 -0.00753 -0.00167 N8 3 0.735232 0.768578 0.123115 11.00000 0.03259 0.01465 = 0.02244 0.00077 -0.00128 0.00216 N9 3 0.783455 0.939055 0.155310 11.00000 0.02866 0.02441 = 0.02150 -0.00116 0.00574 0.00156 N10 3 0.607482 0.858633 -0.043500 11.00000 0.04635 0.03060 = 0.03166 -0.00507 -0.00604 0.00916 N11 3 0.540939 0.708304 0.052124 11.00000 0.03936 0.02307 = 0.03800 -0.00393 -0.00463 0.00293 N12 3 0.824469 0.988477 0.000673 11.00000 0.04196 0.03841 = 0.02190 0.00324 0.00668 0.00209 N13 3 0.847641 1.062663 -0.054940 11.00000 0.04942 0.03431 = 0.03325 0.00307 0.00904 0.00842 N14 3 0.885073 1.136220 -0.100565 11.00000 0.07332 0.05986 = 0.04524 0.01938 0.01716 0.00462 O1 4 0.837335 0.456095 0.036736 11.00000 0.05337 0.03623 = 0.02844 0.00045 -0.00368 0.00692 O2 4 1.011990 0.289857 0.078048 11.00000 0.03977 0.04626 = 0.05913 -0.01816 0.00683 0.01155 O3 4 1.055616 0.364267 0.294849 11.00000 0.04140 0.08130 = 0.03407 0.01924 0.00457 0.01328 O4 4 0.862286 0.914192 0.203385 11.00000 0.03310 0.04157 = 0.02408 -0.00392 -0.00368 0.00150 O5 4 0.741316 1.099420 0.132620 11.00000 0.04566 0.01907 = 0.02890 -0.00090 0.00407 0.00167 O6 4 0.506276 0.744773 -0.013850 11.00000 0.04385 0.03386 = 0.04444 -0.00706 -0.01630 0.00263 HKLF 4 REM 1 in P2(1)/n REM R1 = 0.0480 for 1531 Fo > 4sig(Fo) and 0.0872 for all 2273 data REM 226 parameters refined using 0 restraints END WGHT 0.0462 0.7042 REM Highest difference peak 0.202, deepest hole -0.248, 1-sigma level 0.057 Q1 1 1.1169 0.6194 0.2829 11.00000 0.05 0.20 Q2 1 1.0740 0.1716 0.2786 11.00000 0.05 0.20 Q3 1 0.8362 0.2546 0.0784 11.00000 0.05 0.19 Q4 1 0.7972 0.7224 0.1039 11.00000 0.05 0.19 Q5 1 1.2634 0.3714 0.2830 11.00000 0.05 0.18 Q6 1 0.9575 0.5764 0.1537 11.00000 0.05 0.18 Q7 1 0.9349 0.1694 0.0986 11.00000 0.05 0.18 Q8 1 0.6591 0.8347 -0.0777 11.00000 0.05 0.17 Q9 1 0.9280 0.1521 0.0826 11.00000 0.05 0.17 Q10 1 0.4366 0.6968 -0.0331 11.00000 0.05 0.17 Q11 1 1.5952 0.2212 0.2198 11.00000 0.05 0.16 Q12 1 0.5434 1.0060 -0.1042 11.00000 0.05 0.16 Q13 1 0.7091 0.8015 0.0165 11.00000 0.05 0.16 Q14 1 0.8677 0.4955 0.2911 11.00000 0.05 0.16 Q15 1 0.8429 0.7896 0.2194 11.00000 0.05 0.16 Q16 1 1.5340 0.1778 0.1654 11.00000 0.05 0.16 Q17 1 0.5558 0.9217 -0.0781 11.00000 0.05 0.16 Q18 1 0.9454 0.5851 0.1085 11.00000 0.05 0.16 Q19 1 0.3738 0.7176 0.1034 11.00000 0.05 0.16 Q20 1 1.0056 0.9878 -0.1321 11.00000 0.05 0.15 ; _shelx_res_checksum 62276 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7653(3) 0.5753(4) 0.15345(13) 0.0242(6) Uani 1 1 d . . . . . H1A H 0.6986 0.4749 0.1351 0.029 Uiso 1 1 calc R U . . . H1B H 0.7534 0.5851 0.2019 0.029 Uiso 1 1 calc R U . . . C2 C 1.1382(3) 0.4215(5) 0.20069(15) 0.0354(8) Uani 1 1 d . . . . . C3 C 0.9919(3) 0.4416(4) 0.19538(14) 0.0292(7) Uani 1 1 d . . . . . C4 C 0.7017(3) 0.8859(4) 0.00370(13) 0.0254(7) Uani 1 1 d . . . . . C5 C 0.6595(3) 0.7918(4) 0.06271(13) 0.0231(6) Uani 1 1 d . . . . . N1 N 0.9047(2) 0.5060(3) 0.14243(11) 0.0229(5) Uani 1 1 d . . . . . N2 N 0.9190(3) 0.4100(4) 0.08110(12) 0.0312(6) Uani 1 1 d . . . . . N3 N 1.1768(3) 0.3722(5) 0.26101(13) 0.0469(8) Uani 1 1 d . . . . . N4 N 0.9427(3) 0.4036(4) 0.25321(12) 0.0400(7) Uani 1 1 d . . . . . N5 N 1.2266(3) 0.4491(5) 0.14930(13) 0.0424(7) Uani 1 1 d . . . . . N6 N 1.3503(3) 0.4144(5) 0.16683(13) 0.0406(7) Uani 1 1 d . . . . . N7 N 1.4633(3) 0.3866(5) 0.17428(14) 0.0551(9) Uani 1 1 d . . . . . N8 N 0.7352(2) 0.7686(3) 0.12312(10) 0.0233(5) Uani 1 1 d . . . . . N9 N 0.7835(2) 0.9391(4) 0.15531(11) 0.0247(6) Uani 1 1 d . . . . . N10 N 0.6075(3) 0.8586(4) -0.04350(12) 0.0365(7) Uani 1 1 d . . . . . N11 N 0.5409(3) 0.7083(4) 0.05212(12) 0.0337(6) Uani 1 1 d . . . . . N12 N 0.8245(3) 0.9885(4) 0.00067(11) 0.0339(6) Uani 1 1 d . . . . . N13 N 0.8476(3) 1.0627(4) -0.05494(13) 0.0388(7) Uani 1 1 d . . . . . N14 N 0.8851(4) 1.1362(5) -0.10057(15) 0.0590(9) Uani 1 1 d . . . . . O1 O 0.8373(2) 0.4561(3) 0.03674(10) 0.0395(6) Uani 1 1 d . . . . . O2 O 1.0120(2) 0.2899(4) 0.07805(11) 0.0482(7) Uani 1 1 d . . . . . O3 O 1.0556(2) 0.3643(4) 0.29485(11) 0.0522(7) Uani 1 1 d . . . . . O4 O 0.8623(2) 0.9142(3) 0.20339(9) 0.0331(5) Uani 1 1 d . . . . . O5 O 0.7413(2) 1.0994(3) 0.13262(9) 0.0311(5) Uani 1 1 d . . . . . O6 O 0.5063(2) 0.7448(3) -0.01385(11) 0.0413(6) Uani 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 C1 0.0225(15) 0.0200(15) 0.0308(15) 0.0101(12) 0.0084(12) 0.0025(13) C2 0.0327(18) 0.0398(19) 0.0340(17) 0.0053(15) 0.0039(13) 0.0049(16) C3 0.0312(17) 0.0246(16) 0.0321(16) 0.0027(13) 0.0050(13) 0.0015(14) C4 0.0339(18) 0.0193(15) 0.0227(15) -0.0036(12) -0.0018(13) 0.0109(13) C5 0.0247(16) 0.0173(15) 0.0268(15) -0.0037(12) -0.0029(12) 0.0063(13) N1 0.0243(13) 0.0217(12) 0.0230(12) 0.0001(10) 0.0053(10) 0.0048(11) N2 0.0337(16) 0.0232(14) 0.0374(15) -0.0056(12) 0.0095(12) 0.0027(13) N3 0.0362(17) 0.068(2) 0.0362(16) 0.0132(15) 0.0036(13) 0.0101(15) N4 0.0333(16) 0.0505(19) 0.0364(15) 0.0123(13) 0.0053(12) 0.0052(14) N5 0.0234(15) 0.067(2) 0.0371(15) 0.0083(14) 0.0013(12) 0.0014(14) N6 0.0283(17) 0.059(2) 0.0348(15) -0.0051(14) 0.0005(12) -0.0035(15) N7 0.0299(18) 0.091(3) 0.0434(17) -0.0082(17) -0.0075(14) -0.0017(17) N8 0.0326(14) 0.0146(12) 0.0224(12) 0.0008(10) -0.0013(10) 0.0022(11) N9 0.0287(14) 0.0244(14) 0.0215(13) -0.0012(11) 0.0057(10) 0.0016(11) N10 0.0464(18) 0.0306(15) 0.0317(14) -0.0051(12) -0.0060(13) 0.0092(13) N11 0.0394(17) 0.0231(14) 0.0380(15) -0.0039(11) -0.0046(12) 0.0029(12) N12 0.0420(17) 0.0384(16) 0.0219(13) 0.0032(11) 0.0067(11) 0.0021(13) N13 0.0494(18) 0.0343(16) 0.0332(16) 0.0031(13) 0.0090(13) 0.0084(14) N14 0.073(2) 0.060(2) 0.0452(18) 0.0194(17) 0.0172(17) 0.0046(18) O1 0.0534(15) 0.0362(14) 0.0284(11) 0.0005(10) -0.0037(11) 0.0069(11) O2 0.0398(14) 0.0463(15) 0.0591(15) -0.0182(12) 0.0068(12) 0.0116(13) O3 0.0414(15) 0.0813(19) 0.0341(13) 0.0192(12) 0.0046(11) 0.0133(13) O4 0.0331(12) 0.0416(14) 0.0241(11) -0.0039(9) -0.0037(9) 0.0015(10) O5 0.0457(14) 0.0191(11) 0.0289(11) -0.0009(9) 0.0041(9) 0.0017(10) O6 0.0438(14) 0.0339(13) 0.0444(13) -0.0071(10) -0.0163(11) 0.0026(11) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 C1 N1 112.7(2) . . ? N8 C1 H1A 109.0 . . ? N1 C1 H1A 109.0 . . ? N8 C1 H1B 109.0 . . ? N1 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? N3 C2 N5 124.8(3) . . ? N3 C2 C3 109.5(3) . . ? N5 C2 C3 125.6(3) . . ? N4 C3 N1 120.3(3) . . ? N4 C3 C2 108.8(3) . . ? N1 C3 C2 130.6(3) . . ? N10 C4 N12 128.1(3) . . ? N10 C4 C5 109.2(3) . . ? N12 C4 C5 122.7(2) . . ? N11 C5 N8 121.6(3) . . ? N11 C5 C4 110.1(2) . . ? N8 C5 C4 127.9(3) . . ? C3 N1 N2 116.7(2) . . ? C3 N1 C1 120.9(2) . . ? N2 N1 C1 114.3(2) . . ? O1 N2 O2 126.6(3) . . ? O1 N2 N1 116.5(2) . . ? O2 N2 N1 116.9(3) . . ? C2 N3 O3 104.9(2) . . ? C3 N4 O3 105.3(3) . . ? N6 N5 C2 112.6(3) . . ? N7 N6 N5 171.3(3) . . ? N9 N8 C5 118.1(2) . . ? N9 N8 C1 118.4(2) . . ? C5 N8 C1 123.5(2) . . ? O4 N9 O5 127.0(2) . . ? O4 N9 N8 116.7(2) . . ? O5 N9 N8 116.2(2) . . ? C4 N10 O6 104.4(2) . . ? C5 N11 O6 105.0(2) . . ? N13 N12 C4 115.4(3) . . ? N14 N13 N12 170.5(4) . . ? N4 O3 N3 111.4(2) . . ? N11 O6 N10 111.3(2) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N8 1.447(3) . ? C1 N1 1.458(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N3 1.296(4) . ? C2 N5 1.390(4) . ? C2 C3 1.428(4) . ? C3 N4 1.306(4) . ? C3 N1 1.397(4) . ? C4 N10 1.300(4) . ? C4 N12 1.379(4) . ? C4 C5 1.421(4) . ? C5 N11 1.288(4) . ? C5 N8 1.399(3) . ? N1 N2 1.404(3) . ? N2 O1 1.205(3) . ? N2 O2 1.210(3) . ? N3 O3 1.391(3) . ? N4 O3 1.373(3) . ? N5 N6 1.258(4) . ? N6 N7 1.117(4) . ? N8 N9 1.377(3) . ? N9 O4 1.216(3) . ? N9 O5 1.223(3) . ? N10 O6 1.399(3) . ? N11 O6 1.376(3) . ? N12 N13 1.255(3) . ? N13 N14 1.118(4) . ?