#------------------------------------------------------------------------------ #$Date: 2023-11-22 01:37:46 +0200 (Wed, 22 Nov 2023) $ #$Revision: 287712 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247757.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_7247757 loop_ _publ_author_name 'Zhang, Lingfeng' 'Wang, Yu' 'Wang, Yefeng' 'Liu, Shuai' 'Zhang, Na' 'Yang, Mingmin' 'Ma, Haixia' 'Guo, Zhaoqi' _publ_section_title ; N-methylene-C bridged tetrazole and 1,2,4-triazole energetic salts as promising primary explosives ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE01051A _journal_year 2023 _chemical_formula_moiety 'C4 H3 N11 O4, H4 N O, 2(H2 O)' _chemical_formula_sum 'C4 H11 N12 O7' _chemical_formula_weight 339.25 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _audit_creation_date 2021-03-19 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-05-20 deposited with the CCDC. 2023-11-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.162(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 3.8946(11) _cell_length_b 14.070(4) _cell_length_c 23.813(7) _cell_measurement_reflns_used 3100 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 22.41 _cell_measurement_theta_min 2.90 _cell_volume 1304.0(6) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _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 'olex2.solve (Bourhis et al., 2015)' _diffrn_ambient_temperature 179.97 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1808 _diffrn_reflns_av_unetI/netI 0.1088 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 16456 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.600 _diffrn_reflns_theta_min 2.896 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_T_max 0.7448 _exptl_absorpt_correction_T_min 0.4168 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1680 before and 0.1069 after correction. The Ratio of minimum to maximum transmission is 0.5596. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.728 _exptl_crystal_description cube _exptl_crystal_F_000 700 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.459 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.118 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 2418 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all 0.1721 _refine_ls_R_factor_gt 0.1056 _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^)+(0.0888P)^2^+6.8840P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2375 _refine_ls_wR_factor_ref 0.2709 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1424 _reflns_number_total 2418 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce01051a2.cif _cod_data_source_block a_a _cod_original_cell_volume 1303.9(6) _cod_database_code 7247757 _shelx_shelxl_version_number 2018/3 _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_max 0.997 _shelx_estimated_absorpt_t_min 0.984 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All N(H) groups, All N(H,H) groups At 1.5 times of: All O(H) groups, All O(H,H) groups 2.a Free rotating group: O7(H7A,H7B), O6(H6A,H6B) 2.b Rotating group: N12(H12A,H12B) 2.c Secondary CH2 refined with riding coordinates: C2(H2A,H2B) 2.d Aromatic/amide H refined with riding coordinates: N1(H1) 2.e Idealised tetrahedral OH refined as rotating group: O8(H8) ; _shelx_res_file ; TITL a_a_a.res in P2(1)/c a_a.res created by SHELXL-2018/3 at 20:23:53 on 19-Mar-2021 REM Old TITL A_a in P2/c #13 REM SHELXT solution in P2(1)/c REM R1 0.229, Rweak 0.095, Alpha 0.067, Orientation as input REM Formula found by SHELXT: C17 N2 O4 CELL 0.71073 3.8946 14.0696 23.813 90 92.162 90 ZERR 4 0.0011 0.0041 0.0065 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 16 44 48 28 L.S. 99 PLAN 10 SIZE 0.1 0.1 0.02 TEMP -93.18 MPLA C1 N1 N2 N3 N4 MPLA C3 C4 N7 N8 N9 BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.088800 6.884000 FVAR 0.57131 O3 4 0.582171 0.351687 0.331901 11.00000 0.03407 0.03201 = 0.03621 -0.00152 0.00731 0.00729 O8 4 -0.269281 0.580640 0.466561 11.00000 0.02753 0.04373 = 0.03485 -0.00636 0.00174 -0.00904 AFIX 147 H8 2 -0.207992 0.581333 0.433119 11.00000 -1.50000 AFIX 0 O2 4 -0.055672 0.821270 0.506401 11.00000 0.04246 0.03871 = 0.03284 0.00188 0.00656 0.00311 O4 4 0.543563 0.303981 0.418424 11.00000 0.03256 0.03665 = 0.04031 0.01020 -0.00054 0.00848 AFIX 6 O7 4 0.971262 1.171283 0.336278 11.00000 0.04093 0.03726 = 0.04251 -0.00259 -0.00109 -0.00282 H7A 2 0.900742 1.226682 0.324399 11.00000 -1.50000 H7B 2 0.939681 1.129514 0.309615 11.00000 -1.50000 AFIX 0 N4 3 -0.019336 0.797512 0.319105 11.00000 0.01934 0.03095 = 0.03023 0.00571 0.00355 0.00147 N8 3 0.123964 0.584948 0.275205 11.00000 0.02500 0.01971 = 0.03708 -0.00344 0.00089 -0.00325 O1 4 0.191407 0.935006 0.461891 11.00000 0.05849 0.03546 = 0.04777 -0.00785 0.00717 -0.01612 N1 3 0.270315 0.916818 0.350577 11.00000 0.02245 0.02639 = 0.03770 -0.00223 -0.00039 -0.00437 AFIX 43 H1 2 0.366753 0.960189 0.372634 11.00000 -1.20000 AFIX 0 N9 3 0.270604 0.503233 0.297834 11.00000 0.02298 0.02946 = 0.03466 0.00267 -0.00364 -0.00310 N3 3 0.118213 0.839355 0.274151 11.00000 0.02286 0.02394 = 0.04441 0.00200 -0.00035 0.00477 N5 3 -0.032876 0.808672 0.415748 11.00000 0.02655 0.03702 = 0.02808 0.00255 0.00003 -0.00225 N7 3 -0.000319 0.574106 0.365897 11.00000 0.02272 0.03398 = 0.03012 0.00016 -0.00002 0.00478 N2 3 0.289969 0.910672 0.293600 11.00000 0.02254 0.03047 = 0.03441 0.00561 0.00021 0.00483 N10 3 0.270216 0.433242 0.393707 11.00000 0.02727 0.01970 = 0.03585 0.00019 0.00308 0.00393 N11 3 0.469866 0.360837 0.380073 11.00000 0.02610 0.02403 = 0.03549 0.00302 -0.00255 -0.00540 N6 3 0.040802 0.857275 0.460902 11.00000 0.02837 0.03617 = 0.03489 0.00086 0.00011 0.01054 N12 3 -0.012364 0.624375 0.501612 11.00000 0.02386 0.03135 = 0.03623 -0.00359 -0.00460 -0.00366 AFIX 7 H12A 2 0.190477 0.603009 0.492420 11.00000 -1.20000 H12B 2 -0.018673 0.686536 0.497674 11.00000 -1.20000 AFIX 6 O6 4 0.534127 1.084795 0.413448 11.00000 0.04922 0.07091 = 0.06438 0.00023 0.00809 -0.00789 H6A 2 0.670974 1.111600 0.390202 11.00000 -1.50000 H6B 2 0.661602 1.075017 0.443691 11.00000 -1.50000 AFIX 0 C4 1 0.191517 0.498302 0.353289 11.00000 0.01903 0.02057 = 0.03414 0.00539 -0.00341 -0.00664 C3 1 -0.034184 0.621796 0.317438 11.00000 0.01368 0.03345 = 0.03142 -0.00199 0.00244 -0.00711 C1 1 0.077140 0.844509 0.366155 11.00000 0.01881 0.02046 = 0.03480 0.00348 -0.00574 0.00628 C2 1 -0.231102 0.712772 0.311450 11.00000 0.02202 0.01854 = 0.04146 -0.00069 -0.00159 -0.00109 AFIX 23 H2A 2 -0.345203 0.714821 0.273608 11.00000 -1.20000 H2B 2 -0.412916 0.713558 0.339400 11.00000 -1.20000 AFIX 0 H12C 2 -0.016894 0.604492 0.545287 11.00000 0.09697 HKLF 4 REM a_a_a.res in P2(1)/c REM wR2 = 0.2709, GooF = S = 1.091, Restrained GooF = 1.091 for all data REM R1 = 0.1056 for 1424 Fo > 4sig(Fo) and 0.1721 for all 2418 data REM 220 parameters refined using 0 restraints END WGHT 0.0888 6.8839 REM Highest difference peak 0.459, deepest hole -0.478, 1-sigma level 0.118 Q1 1 0.4084 0.4628 0.2821 11.00000 0.05 0.46 Q2 1 -0.0045 0.6527 0.3815 11.00000 0.05 0.43 Q3 1 -0.2225 0.5676 0.5568 11.00000 0.05 0.42 Q4 1 -0.0207 0.6005 0.4090 11.00000 0.05 0.41 Q5 1 0.0080 0.7402 0.4178 11.00000 0.05 0.40 Q6 1 0.0215 0.7462 0.4730 11.00000 0.05 0.39 Q7 1 0.4327 1.0189 0.3947 11.00000 0.05 0.39 Q8 1 0.9820 1.0921 0.3410 11.00000 0.05 0.36 Q9 1 0.0626 0.8394 0.2274 11.00000 0.05 0.35 Q10 1 0.6280 1.1814 0.4158 11.00000 0.05 0.35 ; _shelx_res_checksum 25131 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O3 O 0.5822(12) 0.3517(4) 0.33190(19) 0.0339(12) Uani 1 1 d . . . . . O8 O -0.2693(11) 0.5806(4) 0.46656(19) 0.0354(12) Uani 1 1 d . . . . . H8 H -0.207992 0.581333 0.433119 0.053 Uiso 1 1 calc GR . . . . O2 O -0.0557(12) 0.8213(4) 0.5064(2) 0.0379(13) Uani 1 1 d . . . . . O4 O 0.5436(12) 0.3040(4) 0.4184(2) 0.0366(12) Uani 1 1 d . . . . . O7 O 0.9713(13) 1.1713(4) 0.3363(2) 0.0403(13) Uani 1 1 d . . . . . H7A H 0.900742 1.226682 0.324399 0.060 Uiso 1 1 d G . . . . H7B H 0.939681 1.129514 0.309615 0.060 Uiso 1 1 d G . . . . N4 N -0.0193(12) 0.7975(4) 0.3191(2) 0.0268(13) Uani 1 1 d . . . . . N8 N 0.1240(13) 0.5849(4) 0.2752(2) 0.0273(13) Uani 1 1 d . . . . . O1 O 0.1914(14) 0.9350(4) 0.4619(2) 0.0471(15) Uani 1 1 d . . . . . N1 N 0.2703(13) 0.9168(4) 0.3506(2) 0.0289(13) Uani 1 1 d . . . . . H1 H 0.366753 0.960189 0.372634 0.035 Uiso 1 1 calc R . . . . N9 N 0.2706(13) 0.5032(4) 0.2978(2) 0.0291(13) Uani 1 1 d . . . . . N3 N 0.1182(13) 0.8394(4) 0.2742(2) 0.0304(14) Uani 1 1 d . . . . . N5 N -0.0329(13) 0.8087(4) 0.4157(2) 0.0306(14) Uani 1 1 d . . . . . N7 N -0.0003(13) 0.5741(4) 0.3659(2) 0.0290(14) Uani 1 1 d . . . . . N2 N 0.2900(13) 0.9107(4) 0.2936(2) 0.0292(14) Uani 1 1 d . . . . . N10 N 0.2702(13) 0.4332(4) 0.3937(2) 0.0276(13) Uani 1 1 d . . . . . N11 N 0.4699(13) 0.3608(4) 0.3801(2) 0.0286(13) Uani 1 1 d . . . . . N6 N 0.0408(14) 0.8573(5) 0.4609(2) 0.0332(14) Uani 1 1 d . . . . . N12 N -0.0124(14) 0.6244(4) 0.5016(2) 0.0306(14) Uani 1 1 d . . . . . H12A H 0.190477 0.603009 0.492420 0.037 Uiso 1 1 d GR . . . . H12B H -0.018673 0.686536 0.497674 0.037 Uiso 1 1 d GR . . . . O6 O 0.5341(15) 1.0848(5) 0.4134(3) 0.0614(17) Uani 1 1 d . . . . . H6A H 0.670974 1.111600 0.390202 0.092 Uiso 1 1 d G . . . . H6B H 0.661602 1.075017 0.443691 0.092 Uiso 1 1 d G . . . . C4 C 0.1915(14) 0.4983(5) 0.3533(3) 0.0247(15) Uani 1 1 d . . . . . C3 C -0.0342(15) 0.6218(5) 0.3174(3) 0.0261(15) Uani 1 1 d . . . . . C1 C 0.0771(15) 0.8445(5) 0.3662(3) 0.0249(15) Uani 1 1 d . . . . . C2 C -0.2311(15) 0.7128(5) 0.3114(3) 0.0274(15) Uani 1 1 d . . . . . H2A H -0.345203 0.714821 0.273608 0.033 Uiso 1 1 calc R . . . . H2B H -0.412916 0.713558 0.339400 0.033 Uiso 1 1 calc R . . . . H12C H -0.02(3) 0.604(8) 0.545(4) 0.10(4) 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 O3 0.034(2) 0.032(3) 0.036(3) -0.002(2) 0.007(2) 0.007(2) O8 0.028(2) 0.044(3) 0.035(3) -0.006(3) 0.002(2) -0.009(2) O2 0.042(3) 0.039(3) 0.033(3) 0.002(2) 0.007(2) 0.003(2) O4 0.033(3) 0.037(3) 0.040(3) 0.010(3) -0.001(2) 0.008(2) O7 0.041(3) 0.037(3) 0.043(3) -0.003(3) -0.001(2) -0.003(3) N4 0.019(3) 0.031(4) 0.030(3) 0.006(3) 0.004(2) 0.001(2) N8 0.025(3) 0.020(3) 0.037(3) -0.003(3) 0.001(2) -0.003(2) O1 0.058(3) 0.035(3) 0.048(3) -0.008(3) 0.007(3) -0.016(3) N1 0.022(3) 0.026(3) 0.038(3) -0.002(3) 0.000(2) -0.004(2) N9 0.023(3) 0.029(4) 0.035(3) 0.003(3) -0.004(2) -0.003(2) N3 0.023(3) 0.024(3) 0.044(4) 0.002(3) 0.000(2) 0.005(2) N5 0.027(3) 0.037(4) 0.028(3) 0.003(3) 0.000(2) -0.002(3) N7 0.023(3) 0.034(4) 0.030(3) 0.000(3) 0.000(2) 0.005(2) N2 0.023(3) 0.030(4) 0.034(3) 0.006(3) 0.000(2) 0.005(2) N10 0.027(3) 0.020(3) 0.036(3) 0.000(3) 0.003(2) 0.004(2) N11 0.026(3) 0.024(3) 0.035(3) 0.003(3) -0.003(3) -0.005(2) N6 0.028(3) 0.036(4) 0.035(4) 0.001(3) 0.000(3) 0.011(3) N12 0.024(3) 0.031(4) 0.036(3) -0.004(3) -0.005(2) -0.004(2) O6 0.049(4) 0.071(5) 0.064(4) 0.000(4) 0.008(3) -0.008(3) C4 0.019(3) 0.021(4) 0.034(4) 0.005(3) -0.003(3) -0.007(3) C3 0.014(3) 0.033(4) 0.031(4) -0.002(3) 0.002(3) -0.007(3) C1 0.019(3) 0.020(4) 0.035(4) 0.003(3) -0.006(3) 0.006(3) C2 0.022(3) 0.019(4) 0.041(4) -0.001(3) -0.002(3) -0.001(3) 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 N12 O8 H8 109.5 . . ? H7A O7 H7B 109.5 . . ? N3 N4 C2 119.8(5) . . ? C1 N4 N3 109.9(5) . . ? C1 N4 C2 130.3(5) . . ? C3 N8 N9 103.3(5) . . ? N2 N1 H1 126.8 . . ? C1 N1 H1 126.8 . . ? C1 N1 N2 106.4(5) . . ? C4 N9 N8 108.2(5) . . ? N2 N3 N4 105.8(5) . . ? N6 N5 C1 117.0(6) . . ? C3 N7 C4 104.1(5) . . ? N3 N2 N1 111.1(5) . . ? N11 N10 C4 117.6(6) . . ? O3 N11 N10 122.1(6) . . ? O4 N11 O3 122.0(6) . . ? O4 N11 N10 115.8(5) . . ? O2 N6 N5 115.8(6) . . ? O1 N6 O2 119.5(6) . . ? O1 N6 N5 124.7(6) . . ? O8 N12 H12A 109.0 . . ? O8 N12 H12B 110.6 . . ? O8 N12 H12C 115(6) . . ? H12A N12 H12B 109.5 . . ? H12A N12 H12C 101.5 . . ? H12B N12 H12C 111.1 . . ? H6A O6 H6B 104.6 . . ? N7 C4 N9 108.8(6) . . ? N7 C4 N10 119.4(6) . . ? N10 C4 N9 131.8(6) . . ? N8 C3 N7 115.5(6) . . ? N8 C3 C2 121.4(6) . . ? N7 C3 C2 123.0(6) . . ? N4 C1 N5 116.9(6) . . ? N1 C1 N4 106.8(6) . . ? N1 C1 N5 136.4(6) . . ? N4 C2 C3 113.7(5) . . ? N4 C2 H2A 108.8 . . ? N4 C2 H2B 108.8 . . ? C3 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? 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 O3 N11 1.250(7) . ? O8 H8 0.8400 . ? O8 N12 1.419(7) . ? O2 N6 1.266(7) . ? O4 N11 1.240(7) . ? O7 H7A 0.8701 . ? O7 H7B 0.8705 . ? N4 N3 1.350(7) . ? N4 C1 1.342(8) . ? N4 C2 1.457(8) . ? N8 N9 1.384(8) . ? N8 C3 1.306(8) . ? O1 N6 1.241(8) . ? N1 H1 0.8800 . ? N1 N2 1.365(8) . ? N1 C1 1.327(8) . ? N9 C4 1.369(8) . ? N3 N2 1.283(8) . ? N5 N6 1.297(8) . ? N5 C1 1.368(8) . ? N7 C4 1.343(8) . ? N7 C3 1.337(8) . ? N10 N11 1.329(7) . ? N10 C4 1.355(8) . ? N12 H12A 0.8806 . ? N12 H12B 0.8798 . ? N12 H12C 1.08(10) . ? O6 H6A 0.8689 . ? O6 H6B 0.8701 . ? C3 C2 1.496(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ?