#------------------------------------------------------------------------------ #$Date: 2024-02-04 13:39:14 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289448 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247756.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_7247756 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_issue 2 _journal_name_full CrystEngComm _journal_page_first 143 _journal_page_last 152 _journal_paper_doi 10.1039/D3CE01051A _journal_volume 26 _journal_year 2024 _chemical_formula_moiety 'C4 H8 N10' _chemical_formula_sum 'C4 H8 N10' _chemical_formula_weight 196.20 _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 dual _audit_creation_date 2020-06-25 _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 101.968(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0488(14) _cell_length_b 13.078(2) _cell_length_c 6.7239(12) _cell_measurement_reflns_used 5386 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 34.657 _cell_measurement_theta_min 2.779 _cell_volume 778.4(2) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_unetI/netI 0.0655 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 10486 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.657 _diffrn_reflns_theta_min 2.301 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_T_max 0.7468 _exptl_absorpt_correction_T_min 0.5615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1407 before and 0.0816 after correction. The Ratio of minimum to maximum transmission is 0.7519. The \l/2 correction factor is 0.00150.' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.674 _exptl_crystal_description needle _exptl_crystal_F_000 408 _refine_diff_density_max 0.516 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.081 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 3276 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0678 _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^)+(0.0542P)^2^+0.6831P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1607 _refine_ls_wR_factor_ref 0.1707 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2677 _reflns_number_total 3276 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce01051a2.cif _cod_data_source_block a _cod_depositor_comments 'Adding full bibliography for 7247754--7247757.cif.' _cod_database_code 7247756 _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. ; _exptl_absorpt_special_details culumn _olex2_refinement_description ; 1. Others Fixed Uiso: H9A(0.025) H10A(0.033) H10B(0.033) H00A(0.023) H00B(0.023) Fixed X: H9A(0.283977) H10A(1.095003) H10B(0.929626) H00A(0.7369) H00B(0.694489) Fixed Y: H9A(0.382438) H10A(0.511774) H10B(0.504841) H00A(0.372823) H00B(0.264718) Fixed Z: H9A(0.160828) H10A(0.769589) H10B(0.762067) H00A(0.816834) H00B(0.720352) ; _shelx_res_file ; TITL a_a.res in P2(1)/c a.res created by SHELXL-2018/3 at 17:31:36 on 25-Jun-2020 REM Old TITL A in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.130, Rweak 0.005, Alpha 0.017, Orientation as input REM Formula found by SHELXT: C14 CELL 0.71073 9.0488 13.078 6.7239 90 101.968 90 ZERR 4 0.0014 0.0021 0.0012 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 16 32 40 L.S. 4 0 0 PLAN 20 TEMP 23 BOND $H list 4 fmap 2 53 ACTA NOHKL REM REM REM WGHT 0.054200 0.683100 FVAR 1.45541 N3 3 0.510603 0.366686 0.435423 11.00000 0.01152 0.01611 = 0.01788 0.00388 0.00438 -0.00101 N4 3 0.899902 0.311075 0.697214 11.00000 0.01289 0.01716 = 0.01982 0.00162 0.00376 0.00205 N9 3 0.338726 0.434310 0.143764 11.00000 0.01655 0.02259 = 0.02161 0.00575 0.00116 -0.00061 AFIX 7 H9A 2 0.283977 0.382438 0.160828 11.00000 -1.20000 AFIX 0 N5 3 0.949759 0.215074 0.669198 11.00000 0.02340 0.02012 = 0.02622 -0.00170 0.00261 0.00590 N1 3 0.720171 0.438668 0.393655 11.00000 0.01530 0.03101 = 0.02292 0.00835 0.00282 -0.00586 N10 3 1.013578 0.476075 0.753667 11.00000 0.02467 0.02140 = 0.03859 -0.00141 0.00974 -0.00514 AFIX 93 H10A 2 1.095003 0.511774 0.769589 11.00000 -1.20000 H10B 2 0.929626 0.504841 0.762067 11.00000 -1.20000 AFIX 0 N8 3 0.415649 0.304592 0.522458 11.00000 0.01534 0.02854 = 0.03091 0.01268 0.00637 -0.00488 N2 3 0.603351 0.467628 0.231362 11.00000 0.01766 0.03128 = 0.02118 0.01002 0.00119 -0.00572 N7 3 1.139143 0.322241 0.699172 11.00000 0.01574 0.03475 = 0.02628 0.00017 0.00599 0.00236 N6 3 1.091119 0.223875 0.670951 11.00000 0.02361 0.03102 = 0.02970 -0.00342 0.00429 0.00996 C00B 1 0.661920 0.378686 0.510807 11.00000 0.01217 0.01728 = 0.01759 0.00199 0.00390 -0.00052 C00C 1 0.479036 0.423451 0.260585 11.00000 0.01553 0.01532 = 0.01679 0.00208 0.00316 -0.00066 C00D 1 1.017503 0.375882 0.715868 11.00000 0.01443 0.02300 = 0.01757 0.00162 0.00456 -0.00063 C00E 1 0.742966 0.329201 0.702127 11.00000 0.01270 0.02557 = 0.02025 0.00693 0.00509 0.00186 AFIX 23 H00A 2 0.736900 0.372823 0.816834 11.00000 -1.20000 H00B 2 0.694489 0.264718 0.720352 11.00000 -1.20000 AFIX 0 H9B 2 0.342449 0.457698 0.023082 11.00000 0.03191 H8A 2 0.344057 0.345095 0.559419 11.00000 0.03506 H8B 2 0.368442 0.258720 0.423710 11.00000 0.04588 HKLF 4 REM a_a.res in P2(1)/c REM wR2 = 0.1707, GooF = S = 1.093, Restrained GooF = 1.093 for all data REM R1 = 0.0678 for 2677 Fo > 4sig(Fo) and 0.0832 for all 3276 data REM 140 parameters refined using 0 restraints END WGHT 0.0540 0.6831 REM Highest difference peak 0.516, deepest hole -0.340, 1-sigma level 0.081 Q1 1 0.9606 0.3430 0.7133 11.00000 0.05 0.52 Q2 1 0.7030 0.3442 0.5856 11.00000 0.05 0.50 Q3 1 1.0829 0.3439 0.7149 11.00000 0.05 0.49 Q4 1 0.4943 0.3931 0.3440 11.00000 0.05 0.46 Q5 1 0.6856 0.4030 0.4349 11.00000 0.05 0.43 Q6 1 0.5388 0.4606 0.2836 11.00000 0.05 0.42 Q7 1 0.5861 0.3468 0.4515 11.00000 0.05 0.42 Q8 1 1.0094 0.4381 0.6791 11.00000 0.05 0.39 Q9 1 1.0660 0.5048 0.6725 11.00000 0.05 0.39 Q10 1 0.9350 0.2753 0.7212 11.00000 0.05 0.37 Q11 1 0.6019 0.4947 0.1471 11.00000 0.05 0.36 Q12 1 0.4098 0.4036 0.1941 11.00000 0.05 0.36 Q13 1 1.0161 0.4238 0.7405 11.00000 0.05 0.33 Q14 1 0.8211 0.3342 0.6914 11.00000 0.05 0.31 Q15 1 0.5795 0.3918 0.4770 11.00000 0.05 0.31 Q16 1 0.8868 0.1788 0.6195 11.00000 0.05 0.28 Q17 1 0.4762 0.2599 0.5368 11.00000 0.05 0.28 Q18 1 0.3931 0.4568 0.2126 11.00000 0.05 0.28 Q19 1 0.8397 0.3234 0.7343 11.00000 0.05 0.27 Q20 1 1.1189 0.1810 0.6146 11.00000 0.05 0.26 ; _shelx_res_checksum 98350 _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 N3 N 0.51060(13) 0.36669(9) 0.43542(18) 0.0150(2) Uani 1 1 d . . . . . N4 N 0.89990(13) 0.31108(9) 0.69721(19) 0.0166(2) Uani 1 1 d . . . . . N9 N 0.33873(15) 0.43431(11) 0.1438(2) 0.0207(3) Uani 1 1 d . . . . . H9A H 0.283977 0.382438 0.160828 0.025 Uiso 1 1 d GR . . . . N5 N 0.94976(16) 0.21507(11) 0.6692(2) 0.0236(3) Uani 1 1 d . . . . . N1 N 0.72017(15) 0.43867(11) 0.3937(2) 0.0232(3) Uani 1 1 d . . . . . N10 N 1.01358(17) 0.47607(11) 0.7537(3) 0.0278(3) Uani 1 1 d . . . . . H10A H 1.095003 0.511774 0.769589 0.033 Uiso 1 1 calc R . . . . H10B H 0.929626 0.504841 0.762067 0.033 Uiso 1 1 calc R . . . . N8 N 0.41565(15) 0.30459(12) 0.5225(2) 0.0247(3) Uani 1 1 d . . . . . N2 N 0.60335(15) 0.46763(12) 0.2314(2) 0.0238(3) Uani 1 1 d . . . . . N7 N 1.13914(15) 0.32224(12) 0.6992(2) 0.0254(3) Uani 1 1 d . . . . . N6 N 1.09112(17) 0.22387(12) 0.6710(2) 0.0283(3) Uani 1 1 d . . . . . C2 C 0.66192(15) 0.37869(11) 0.5108(2) 0.0156(2) Uani 1 1 d . . . . . C1 C 0.47904(15) 0.42345(10) 0.2606(2) 0.0159(2) Uani 1 1 d . . . . . C4 C 1.01750(16) 0.37588(12) 0.7159(2) 0.0182(3) Uani 1 1 d . . . . . C3 C 0.74297(15) 0.32920(12) 0.7021(2) 0.0193(3) Uani 1 1 d . . . . . H00A H 0.736900 0.372823 0.816834 0.023 Uiso 1 1 calc R . . . . H00B H 0.694489 0.264718 0.720352 0.023 Uiso 1 1 calc R . . . . H9B H 0.342(3) 0.4577(19) 0.023(4) 0.032(6) Uiso 1 1 d . . . . . H8A H 0.344(3) 0.3451(19) 0.559(4) 0.035(6) Uiso 1 1 d . . . . . H8B H 0.368(3) 0.259(2) 0.424(5) 0.046(8) 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 N3 0.0115(4) 0.0161(5) 0.0179(5) 0.0039(4) 0.0044(4) -0.0010(4) N4 0.0129(5) 0.0172(5) 0.0198(5) 0.0016(4) 0.0038(4) 0.0021(4) N9 0.0165(5) 0.0226(6) 0.0216(6) 0.0058(5) 0.0012(4) -0.0006(4) N5 0.0234(6) 0.0201(6) 0.0262(6) -0.0017(5) 0.0026(5) 0.0059(5) N1 0.0153(5) 0.0310(7) 0.0229(6) 0.0084(5) 0.0028(4) -0.0059(5) N10 0.0247(6) 0.0214(6) 0.0386(8) -0.0014(6) 0.0097(6) -0.0051(5) N8 0.0153(5) 0.0285(7) 0.0309(7) 0.0127(5) 0.0064(5) -0.0049(5) N2 0.0177(5) 0.0313(7) 0.0212(6) 0.0100(5) 0.0012(4) -0.0057(5) N7 0.0157(5) 0.0348(8) 0.0263(6) 0.0002(5) 0.0060(5) 0.0024(5) N6 0.0236(6) 0.0310(7) 0.0297(7) -0.0034(6) 0.0043(5) 0.0100(6) C2 0.0122(5) 0.0173(6) 0.0176(5) 0.0020(4) 0.0039(4) -0.0005(4) C1 0.0155(5) 0.0153(5) 0.0168(5) 0.0021(4) 0.0032(4) -0.0007(4) C4 0.0144(5) 0.0230(6) 0.0176(6) 0.0016(5) 0.0046(4) -0.0006(5) C3 0.0127(5) 0.0256(7) 0.0203(6) 0.0069(5) 0.0051(4) 0.0019(5) 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' 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 C2 N3 N8 124.58(12) . . ? C2 N3 C1 105.70(11) . . ? C1 N3 N8 129.66(12) . . ? N5 N4 C3 120.64(13) . . ? C4 N4 N5 108.40(12) . . ? C4 N4 C3 130.96(13) . . ? H9A N9 H9B 122.2 . . ? C1 N9 H9A 109.6 . . ? C1 N9 H9B 111.3(17) . . ? N6 N5 N4 105.95(13) . . ? C2 N1 N2 107.42(12) . . ? H10A N10 H10B 120.0 . . ? C4 N10 H10A 120.0 . . ? C4 N10 H10B 120.0 . . ? N3 N8 H8A 108.1(16) . . ? N3 N8 H8B 107.9(19) . . ? H8A N8 H8B 109(2) . . ? C1 N2 N1 107.14(12) . . ? C4 N7 N6 105.37(13) . . ? N5 N6 N7 112.08(13) . . ? N3 C2 C3 123.10(12) . . ? N1 C2 N3 110.23(12) . . ? N1 C2 C3 126.66(13) . . ? N9 C1 N3 123.92(13) . . ? N2 C1 N3 109.50(12) . . ? N2 C1 N9 126.52(13) . . ? N10 C4 N4 125.69(14) . . ? N7 C4 N4 108.20(14) . . ? N7 C4 N10 126.05(14) . . ? N4 C3 C2 111.17(11) . . ? N4 C3 H00A 109.4 . . ? N4 C3 H00B 109.4 . . ? C2 C3 H00A 109.4 . . ? C2 C3 H00B 109.4 . . ? H00A C3 H00B 108.0 . . ? 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 N3 N8 1.3960(17) . ? N3 C2 1.3669(17) . ? N3 C1 1.3695(18) . ? N4 N5 1.3604(18) . ? N4 C4 1.3458(19) . ? N4 C3 1.4469(18) . ? N9 H9A 0.8616 . ? N9 C1 1.3548(19) . ? N9 H9B 0.87(3) . ? N5 N6 1.282(2) . ? N1 N2 1.4047(19) . ? N1 C2 1.2984(18) . ? N10 H10A 0.8600 . ? N10 H10B 0.8600 . ? N10 C4 1.337(2) . ? N8 H8A 0.91(3) . ? N8 H8B 0.93(3) . ? N2 C1 1.3151(18) . ? N7 N6 1.359(2) . ? N7 C4 1.3295(19) . ? C2 C3 1.490(2) . ? C3 H00A 0.9700 . ? C3 H00B 0.9700 . ?