#------------------------------------------------------------------------------ #$Date: 2021-09-15 03:17:33 +0300 (Wed, 15 Sep 2021) $ #$Revision: 269144 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060954.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_7060954 loop_ _publ_author_name 'Chen, Dongxu' 'Zhao, Jiangshan' 'Yang, Hongwei' 'Gu, Hao' 'Cheng, Guangbin' _publ_section_title ; Introduction of the acylamino group to bridged bis(nitroamino-1,2,4-triazole): a strategy for tuning the sensitivity of energetic materials ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03551G _journal_year 2021 _chemical_formula_moiety 'C5 H6 N10 O3, 2(H2 O)' _chemical_formula_sum 'C5 H10 N10 O5' _chemical_formula_weight 290.23 _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 mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-08-17 deposited with the CCDC. 2021-08-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.745(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9197(14) _cell_length_b 7.1740(7) _cell_length_c 16.673(2) _cell_measurement_reflns_used 849 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.02 _cell_measurement_theta_min 2.79 _cell_volume 1136.2(2) _computing_data_collection APEX3 _computing_molecular_graphics Diamond _computing_publication_material olex _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution SHELXS-2014/7 _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'PHOTON 2 CMOS detector' _diffrn_measurement_method 'omega scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0961 _diffrn_reflns_av_unetI/netI 0.0888 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 6638 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.643 _diffrn_reflns_theta_min 3.113 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2014)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.697 _exptl_crystal_description sheet _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.230 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.346 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 224 _refine_ls_number_reflns 2119 _refine_ls_number_restraints 23 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.1204 _refine_ls_R_factor_gt 0.0522 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.5497P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1276 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1232 _reflns_number_total 2119 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03551g2.cif _cod_data_source_block 1 _cod_original_cell_volume 1136.2(3) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7060954 _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 0.967 _shelx_estimated_absorpt_t_max 0.997 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1 in P2(1)/n CELL 0.71073 9.9197 7.1740 16.6732 90.000 106.745 90.000 ZERR 4.00 0.0014 0.0007 0.0023 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 40 40 20 L.S. 10 BOND $h acta size 0.23 0.11 0.02 FMAP 2 PLAN 20 simu .02 .03 o5 o5' dfix .82 o4 h4c o4 h4d o5 h5c o5 h5d o5' h5'c o5 h5'd sadi h5c h5d h5'c h5'd sadi .02 n2 h2a n6 h6a n10 h10a n10 h10b n8 h8a TEMP -100.150 WGHT 0.043772 0.549725 FVAR 0.25918 0.75003 MOLE 1 C1 1 1.011270 0.221632 1.026479 11.00000 0.02009 0.02663 = 0.02075 -0.00182 0.00301 -0.00133 C2 1 0.829265 0.297150 0.932008 11.00000 0.02134 0.02987 = 0.02169 -0.00044 0.00438 0.00222 C4 1 0.678879 0.329890 0.887103 11.00000 0.02614 0.03735 = 0.02386 -0.00127 0.00302 0.00374 C6 1 0.417699 0.302000 0.721678 11.00000 0.02329 0.04605 = 0.02568 -0.00430 0.00491 -0.00214 C7 1 0.457756 0.601524 0.745921 11.00000 0.03394 0.03990 = 0.03459 0.00160 0.00296 -0.00248 AFIX 43 H7 2 0.504978 0.714923 0.765931 11.00000 -1.20000 AFIX 0 N1 3 0.930618 0.343845 0.898461 11.00000 0.02502 0.03131 = 0.01909 0.00054 0.00356 -0.00095 N2 3 1.047631 0.295296 0.961099 11.00000 0.01996 0.03549 = 0.02140 0.00174 0.00212 -0.00108 H2A 2 1.132976 0.316753 0.958113 11.00000 -1.20000 N3 3 0.870625 0.222618 1.010125 11.00000 0.02074 0.03317 = 0.02121 0.00079 0.00313 0.00031 N4 3 1.092088 0.152228 1.102407 11.00000 0.01781 0.03629 = 0.02315 0.00178 0.00102 0.00275 N5 3 1.228118 0.158259 1.116770 11.00000 0.02523 0.03500 = 0.02580 -0.00242 0.00355 0.00148 N6 3 0.653114 0.388463 0.806854 11.00000 0.01933 0.04974 = 0.02057 0.00145 0.00265 0.00269 H6A 2 0.712394 0.388389 0.776355 11.00000 -1.20000 N7 3 0.327496 0.589371 0.697811 11.00000 0.04266 0.04306 = 0.04684 0.00502 0.01146 0.00151 N8 3 0.303722 0.400701 0.684266 11.00000 0.02443 0.04763 = 0.03356 -0.00077 0.00156 0.00019 H8A 2 0.223192 0.379753 0.643318 11.00000 -1.20000 N9 3 0.515199 0.430063 0.762970 11.00000 0.02166 0.04329 = 0.02359 0.00205 0.00030 0.00177 N10 3 0.436075 0.120091 0.722518 11.00000 0.03098 0.03886 = 0.04584 -0.00569 0.00286 -0.00130 H10A 2 0.514988 0.067582 0.752678 11.00000 -1.20000 H10B 2 0.370009 0.053177 0.686651 11.00000 -1.20000 O1 4 1.288501 0.228198 1.066673 11.00000 0.02388 0.06416 = 0.03036 0.01218 0.00686 -0.00180 O2 4 1.303697 0.092106 1.187356 11.00000 0.02556 0.05100 = 0.02363 0.00660 -0.00138 0.00647 O3 4 0.582742 0.306473 0.918915 11.00000 0.02468 0.07078 = 0.03315 0.01549 0.00808 0.00483 O4 4 0.225137 0.915512 0.604407 11.00000 0.03629 0.05742 = 0.05384 -0.01071 0.01510 -0.00478 H4C 2 0.209685 0.812782 0.624497 11.00000 -1.20000 H4D 2 0.162298 0.990617 0.583984 11.00000 -1.20000 part 1 O5 4 1.572028 0.241681 1.077217 21.00000 0.02424 0.08166 = 0.02951 0.00650 0.00523 0.00340 H5C 2 1.487221 0.251433 1.073163 21.00000 -1.20000 H5D 2 1.577779 0.251441 1.028853 21.00000 -1.20000 part 2 O5' 4 1.560593 0.119924 1.064441 -21.00000 0.04350 0.09335 = 0.05139 0.01807 0.00008 -0.01514 H5'C 2 1.481916 0.087956 1.066148 -21.00000 -1.20000 H5'D 2 1.560086 0.190638 1.031514 -21.00000 -1.20000 part 0 HKLF 4 REM 1 in P2(1)/n REM R1 = 0.0522 for 1232 Fo > 4sig(Fo) and 0.1204 for all 2119 data REM 224 parameters refined using 23 restraints END WGHT 0.0641 0.0866 REM Highest difference peak 0.346, deepest hole -0.255, 1-sigma level 0.060 Q1 1 0.2638 0.5136 0.6193 11.00000 0.05 0.35 Q2 1 0.1479 0.9130 0.6904 11.00000 0.05 0.25 Q3 1 0.8598 0.1451 1.0339 11.00000 0.05 0.23 Q4 1 1.3382 0.0747 1.1583 11.00000 0.05 0.22 Q5 1 0.8861 0.3241 0.9169 11.00000 0.05 0.21 Q6 1 1.0354 0.2556 1.0017 11.00000 0.05 0.21 Q7 1 0.9614 0.3617 1.0652 11.00000 0.05 0.20 Q8 1 0.4712 0.3764 0.8599 11.00000 0.05 0.20 Q9 1 0.5849 0.4089 0.7800 11.00000 0.05 0.19 Q10 1 0.7029 0.4967 0.8377 11.00000 0.05 0.19 Q11 1 0.3428 0.5302 0.5789 11.00000 0.05 0.19 Q12 1 0.2787 0.9849 0.6525 11.00000 0.05 0.19 Q13 1 0.9300 0.1906 1.0031 11.00000 0.05 0.19 Q14 1 0.4941 0.4218 0.8256 11.00000 0.05 0.18 Q15 1 0.8060 0.5869 0.7733 11.00000 0.05 0.18 Q16 1 0.2986 0.0729 0.6233 11.00000 0.05 0.18 Q17 1 0.9396 0.4315 0.8936 11.00000 0.05 0.18 Q18 1 0.2476 0.7526 0.6233 11.00000 0.05 0.18 Q19 1 0.6244 0.3428 0.9016 11.00000 0.05 0.18 Q20 1 0.2292 1.1512 0.6149 11.00000 0.05 0.17 ; _shelx_res_checksum 14117 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 1.0113(3) 0.2216(5) 1.0265(2) 0.0231(8) Uani 1 1 d . . . . . C2 C 0.8293(3) 0.2971(5) 0.9320(2) 0.0247(8) Uani 1 1 d . . . . . C4 C 0.6789(4) 0.3299(5) 0.8871(2) 0.0300(9) Uani 1 1 d . . . . . C6 C 0.4177(4) 0.3020(6) 0.7217(2) 0.0321(9) Uani 1 1 d . . . . . C7 C 0.4578(4) 0.6015(6) 0.7459(2) 0.0376(10) Uani 1 1 d . . . . . H7 H 0.5050 0.7149 0.7659 0.045 Uiso 1 1 calc R U . . . N1 N 0.9306(3) 0.3438(4) 0.89846(17) 0.0257(7) Uani 1 1 d . . . . . N2 N 1.0476(3) 0.2953(4) 0.96110(18) 0.0264(7) Uani 1 1 d D . . . . H2A H 1.133(3) 0.317(5) 0.958(2) 0.032 Uiso 1 1 d D U . . . N3 N 0.8706(3) 0.2226(4) 1.01012(17) 0.0257(7) Uani 1 1 d . . . . . N4 N 1.0921(3) 0.1522(4) 1.10241(18) 0.0268(7) Uani 1 1 d . . . . . N5 N 1.2281(3) 0.1583(4) 1.11677(19) 0.0295(7) Uani 1 1 d . . . . . N6 N 0.6531(3) 0.3885(4) 0.80685(18) 0.0305(7) Uani 1 1 d D . . . . H6A H 0.712(3) 0.388(5) 0.776(2) 0.037 Uiso 1 1 d D U . . . N7 N 0.3275(3) 0.5894(5) 0.6978(2) 0.0445(9) Uani 1 1 d . . . . . N8 N 0.3037(3) 0.4007(5) 0.6843(2) 0.0366(8) Uani 1 1 d D . . . . H8A H 0.223(3) 0.380(5) 0.6433(19) 0.044 Uiso 1 1 d D U . . . N9 N 0.5152(3) 0.4301(4) 0.76297(18) 0.0308(7) Uani 1 1 d . . . . . N10 N 0.4361(3) 0.1201(5) 0.7225(2) 0.0403(8) Uani 1 1 d D . . . . H10A H 0.515(3) 0.068(5) 0.753(2) 0.048 Uiso 1 1 d D U . . . H10B H 0.370(3) 0.053(5) 0.687(2) 0.048 Uiso 1 1 d D U . . . O1 O 1.2885(2) 0.2282(4) 1.06667(16) 0.0397(7) Uani 1 1 d . . . . . O2 O 1.3037(2) 0.0921(4) 1.18736(15) 0.0352(6) Uani 1 1 d . . . . . O3 O 0.5827(3) 0.3065(4) 0.91892(16) 0.0429(7) Uani 1 1 d . . . . . O4 O 0.2251(3) 0.9155(4) 0.6044(2) 0.0487(8) Uani 1 1 d D . . . . H4C H 0.210(5) 0.813(4) 0.624(3) 0.058 Uiso 1 1 d D U . . . H4D H 0.162(4) 0.991(5) 0.584(3) 0.058 Uiso 1 1 d D U . . . O5 O 1.5720(5) 0.2417(15) 1.0772(3) 0.046(2) Uani 0.75(2) 1 d D U P A 1 H5C H 1.487(3) 0.251(9) 1.073(4) 0.055 Uiso 0.75(2) 1 d D U P A 1 H5D H 1.578(8) 0.251(9) 1.029(2) 0.055 Uiso 0.75(2) 1 d D U P A 1 O5' O 1.5606(18) 0.120(5) 1.0644(13) 0.066(6) Uani 0.25(2) 1 d D U P A 2 H5'C H 1.482(9) 0.09(3) 1.066(13) 0.079 Uiso 0.25(2) 1 d D U P A 2 H5'D H 1.56(3) 0.19(3) 1.032(9) 0.079 Uiso 0.25(2) 1 d D U P A 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 C1 0.0201(18) 0.0266(19) 0.0207(19) -0.0018(14) 0.0030(15) -0.0013(14) C2 0.0213(17) 0.0299(19) 0.0217(19) -0.0004(15) 0.0044(15) 0.0022(15) C4 0.0261(19) 0.037(2) 0.024(2) -0.0013(16) 0.0030(16) 0.0037(16) C6 0.0233(19) 0.046(3) 0.026(2) -0.0043(18) 0.0049(16) -0.0021(17) C7 0.034(2) 0.040(2) 0.035(2) 0.0016(19) 0.0030(19) -0.0025(18) N1 0.0250(15) 0.0313(17) 0.0191(16) 0.0005(13) 0.0036(13) -0.0009(12) N2 0.0200(16) 0.0355(17) 0.0214(16) 0.0017(13) 0.0021(13) -0.0011(13) N3 0.0207(15) 0.0332(17) 0.0212(16) 0.0008(13) 0.0031(12) 0.0003(13) N4 0.0178(15) 0.0363(18) 0.0232(17) 0.0018(13) 0.0010(12) 0.0028(12) N5 0.0252(16) 0.0350(17) 0.0258(17) -0.0024(14) 0.0036(14) 0.0015(13) N6 0.0193(16) 0.050(2) 0.0206(17) 0.0015(15) 0.0026(13) 0.0027(14) N7 0.043(2) 0.043(2) 0.047(2) 0.0050(17) 0.0115(18) 0.0015(16) N8 0.0244(17) 0.048(2) 0.034(2) -0.0008(17) 0.0016(14) 0.0002(16) N9 0.0217(16) 0.0433(19) 0.0236(17) 0.0021(14) 0.0003(14) 0.0018(14) N10 0.0310(19) 0.039(2) 0.046(2) -0.0057(17) 0.0029(16) -0.0013(15) O1 0.0239(13) 0.0642(19) 0.0304(15) 0.0122(13) 0.0069(12) -0.0018(12) O2 0.0256(13) 0.0510(16) 0.0236(14) 0.0066(13) -0.0014(11) 0.0065(12) O3 0.0247(14) 0.071(2) 0.0332(16) 0.0155(14) 0.0081(12) 0.0048(13) O4 0.0363(17) 0.057(2) 0.054(2) -0.0107(17) 0.0151(15) -0.0048(15) O5 0.024(2) 0.082(6) 0.030(2) 0.007(3) 0.0052(19) 0.003(3) O5' 0.044(8) 0.093(15) 0.051(9) 0.018(10) 0.000(7) -0.015(10) 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 N3 C1 N2 109.7(3) . . ? N3 C1 N4 118.9(3) . . ? N2 C1 N4 131.4(3) . . ? N1 C2 N3 116.6(3) . . ? N1 C2 C4 121.4(3) . . ? N3 C2 C4 121.9(3) . . ? O3 C4 N6 121.3(3) . . ? O3 C4 C2 123.6(3) . . ? N6 C4 C2 115.1(3) . . ? N10 C6 N8 129.0(4) . . ? N10 C6 N9 125.8(3) . . ? N8 C6 N9 105.1(3) . . ? N7 C7 N9 110.4(3) . . ? N7 C7 H7 124.8 . . ? N9 C7 H7 124.8 . . ? C2 N1 N2 101.2(3) . . ? C1 N2 N1 110.6(3) . . ? C1 N2 H2A 127(2) . . ? N1 N2 H2A 122(2) . . ? C1 N3 C2 101.9(3) . . ? N5 N4 C1 117.0(3) . . ? O1 N5 O2 119.2(3) . . ? O1 N5 N4 123.7(3) . . ? O2 N5 N4 117.1(3) . . ? C4 N6 N9 117.7(3) . . ? C4 N6 H6A 127(2) . . ? N9 N6 H6A 115(2) . . ? C7 N7 N8 104.9(3) . . ? C6 N8 N7 111.3(3) . . ? C6 N8 H8A 136(3) . . ? N7 N8 H8A 111(3) . . ? C7 N9 C6 108.2(3) . . ? C7 N9 N6 126.9(3) . . ? C6 N9 N6 124.7(3) . . ? C6 N10 H10A 122(3) . . ? C6 N10 H10B 117(3) . . ? H10A N10 H10B 121(4) . . ? H4C O4 H4D 122(5) . . ? H5C O5 H5D 105(7) . . ? H5'C O5' H5'D 114(10) . . ? 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 N3 1.342(4) . ? C1 N2 1.351(4) . ? C1 N4 1.381(4) . ? C2 N1 1.327(4) . ? C2 N3 1.357(4) . ? C2 C4 1.482(5) . ? C4 O3 1.229(4) . ? C4 N6 1.355(4) . ? C6 N10 1.317(5) . ? C6 N8 1.328(5) . ? C6 N9 1.367(5) . ? C7 N7 1.313(5) . ? C7 N9 1.351(5) . ? C7 H7 0.9500 . ? N1 N2 1.364(4) . ? N2 H2A 0.88(2) . ? N4 N5 1.301(4) . ? N5 O1 1.264(4) . ? N5 O2 1.290(4) . ? N6 N9 1.385(4) . ? N6 H6A 0.88(2) . ? N7 N8 1.381(4) . ? N8 H8A 0.90(2) . ? N10 H10A 0.88(2) . ? N10 H10B 0.89(2) . ? O4 H4C 0.842(19) . ? O4 H4D 0.820(19) . ? O5 H5C 0.83(2) . ? O5 H5D 0.83(2) . ? O5' H5'C 0.82(2) . ? O5' H5'D 0.7(2) . ?