#------------------------------------------------------------------------------ #$Date: 2023-03-19 01:49:00 +0200 (Sun, 19 Mar 2023) $ #$Revision: 281942 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/71/26/7712654.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_7712654 loop_ _publ_author_name 'Jiang, Xiue' 'Yang, Yalin' 'Du, Huiying' 'Yang, Bo' 'Tang, Pengfei' 'Wu, Bo' 'Ma, Congming' _publ_section_title ; Triazene Bridged Energetic Materials Based on Nitrotriazole: Synthesis, Characterization and Laser Ignited Combustion Performance ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D2DT04007G _journal_year 2023 _chemical_formula_sum 'C4 H7 N11 O6' _chemical_formula_weight 305.21 _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 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2022-12-12 deposited with the CCDC. 2023-03-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.482(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.4637(5) _cell_length_b 16.3279(7) _cell_length_c 6.8604(3) _cell_measurement_reflns_used 9881 _cell_measurement_temperature 146(2) _cell_measurement_theta_max 27.51 _cell_measurement_theta_min 2.49 _cell_volume 1148.64(9) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _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 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 146(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _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 0.0495 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 34305 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.504 _diffrn_reflns_theta_min 2.345 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.765 _exptl_crystal_description block _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.140 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.266 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2636 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0312 _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^)+(0.0511P)^2^+0.3231P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0855 _refine_ls_wR_factor_ref 0.0890 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2246 _reflns_number_total 2636 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2dt04007g2.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7712654 _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_min 0.978 _shelx_estimated_absorpt_t_max 0.981 _shelx_res_file ; TITL 220720_4406_JXE_0ma_a.res in P2(1)/c 220720_4406_JXE_0ma.res created by SHELXL-2018/3 at 15:15:31 on 29-Jul-2022 CELL 0.71073 10.4637 16.3279 6.8604 90.000 101.482 90.000 ZERR 4.000 0.0005 0.0007 0.0003 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 16 28 44 24 L.S. 10 ACTA BOND FMAP 2 PLAN 20 SIZE 0.14 0.13 0.12 TEMP -127.150 WGHT 0.051100 0.323100 FVAR 0.08509 C1 1 0.735685 0.365883 0.605318 11.00000 0.01631 0.01422 = 0.02200 -0.00085 0.00665 0.00134 C2 1 0.674793 0.480703 0.665865 11.00000 0.01622 0.01455 = 0.01785 0.00023 0.00447 0.00107 C3 1 0.651090 0.752689 0.700742 11.00000 0.01928 0.01453 = 0.01587 -0.00053 0.00416 0.00206 C4 1 0.771069 0.847711 0.656985 11.00000 0.01944 0.01619 = 0.01991 -0.00039 0.00350 -0.00054 N1 3 0.739298 0.277594 0.582902 11.00000 0.02113 0.01528 = 0.03010 -0.00179 0.00894 0.00115 N2 3 0.828835 0.411622 0.562442 11.00000 0.01867 0.01465 = 0.02896 -0.00042 0.00894 0.00134 N3 3 0.636954 0.402985 0.670172 11.00000 0.01699 0.01320 = 0.02244 -0.00058 0.00740 0.00013 N4 3 0.787919 0.487293 0.603297 11.00000 0.01804 0.01254 = 0.02728 -0.00015 0.00929 -0.00024 AFIX 43 H4 2 0.829026 0.533422 0.590774 11.00000 -1.20000 AFIX 0 N5 3 0.606245 0.546966 0.714423 11.00000 0.01834 0.01295 = 0.02647 -0.00045 0.01064 -0.00023 AFIX 43 H5 2 0.533804 0.541804 0.760096 11.00000 -1.20000 AFIX 0 N6 3 0.657920 0.619482 0.687009 11.00000 0.01955 0.01369 = 0.01944 -0.00021 0.00493 0.00062 N7 3 0.589764 0.678740 0.727396 11.00000 0.02017 0.01470 = 0.02130 -0.00049 0.00699 0.00144 N8 3 0.591837 0.824142 0.723118 11.00000 0.01744 0.01420 = 0.02386 -0.00077 0.00655 0.00116 AFIX 43 H8 2 0.513908 0.829049 0.751894 11.00000 -1.20000 AFIX 0 N9 3 0.669318 0.887117 0.695006 11.00000 0.02048 0.01469 = 0.02468 -0.00030 0.00458 -0.00088 N10 3 0.767898 0.765580 0.657230 11.00000 0.01874 0.01585 = 0.01892 -0.00047 0.00535 0.00033 N11 3 0.881326 0.893619 0.613295 11.00000 0.02260 0.01993 = 0.03000 0.00018 0.00684 -0.00206 O1 4 0.647009 0.239154 0.623534 11.00000 0.02888 0.01606 = 0.04801 -0.00044 0.01681 -0.00443 PART 1 O2 4 0.831472 0.247635 0.524970 11.00000 0.02925 0.02242 = 0.05538 -0.00765 0.02108 0.00518 PART 0 O3 4 0.873492 0.968689 0.618122 11.00000 0.03765 0.01792 = 0.06766 0.00387 0.02132 -0.00423 PART 1 O4 4 0.972159 0.854816 0.576203 11.00000 0.02542 0.03201 = 0.04809 -0.00503 0.01717 -0.00092 PART 0 O5 4 0.385114 0.560329 0.855896 11.00000 0.02875 0.01612 = 0.05699 -0.00430 0.02081 -0.00368 O6 4 0.924724 0.623092 0.564729 11.00000 0.01908 0.01876 = 0.04373 -0.00140 0.01409 -0.00116 AFIX 3 H5A 2 0.351390 0.606886 0.869682 11.00000 -1.50000 H6A 2 0.899400 0.668746 0.603002 11.00000 -1.50000 H5B 2 0.325650 0.523486 0.842952 11.00000 -1.50000 H6B 2 1.003810 0.623206 0.551642 11.00000 -1.50000 AFIX 0 HKLF 4 REM 220720_4406_JXE_0ma_a.res in P2(1)/c REM wR2 = 0.089037, GooF = S = 1.03670, Restrained GooF = 1.03670 for all data REM R1 = 0.031231 for 2246 Fo > 4sig(Fo) and 0.037635 for all 2636 data REM 190 parameters refined using 0 restraints END WGHT 0.0459 0.3604 REM Highest difference peak 0.266, deepest hole -0.313, 1-sigma level 0.047 Q1 1 0.7388 0.3241 0.5949 11.00000 0.05 0.27 Q2 1 0.6553 0.4391 0.6915 11.00000 0.05 0.22 Q3 1 0.7747 0.8019 0.6353 11.00000 0.05 0.22 Q4 1 0.6112 0.7829 0.7026 11.00000 0.05 0.21 Q5 1 0.5297 0.6747 0.7438 11.00000 0.05 0.21 Q6 1 0.6798 0.3818 0.6316 11.00000 0.05 0.20 Q7 1 0.6415 0.5145 0.6920 11.00000 0.05 0.19 Q8 1 0.7208 0.7558 0.7097 11.00000 0.05 0.18 Q9 1 0.7473 0.4825 0.6755 11.00000 0.05 0.18 Q10 1 0.8182 0.8662 0.6240 11.00000 0.05 0.17 Q11 1 0.9611 0.6133 0.6947 11.00000 0.05 0.17 Q12 1 0.5830 0.3810 0.7154 11.00000 0.05 0.16 Q13 1 0.6259 0.7143 0.7214 11.00000 0.05 0.16 Q14 1 0.7803 0.3833 0.5667 11.00000 0.05 0.16 Q15 1 0.7957 0.3810 0.6238 11.00000 0.05 0.16 Q16 1 0.7161 0.8654 0.6302 11.00000 0.05 0.16 Q17 1 0.6404 0.9211 0.6306 11.00000 0.05 0.15 Q18 1 0.4278 0.5630 0.7445 11.00000 0.05 0.15 Q19 1 0.6796 0.9226 0.7566 11.00000 0.05 0.14 Q20 1 0.8924 0.3980 0.5628 11.00000 0.05 0.14 ; _shelx_res_checksum 37301 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 C1 C 0.73569(11) 0.36588(7) 0.60532(17) 0.0171(2) Uani 1 1 d . . . . . C2 C 0.67479(11) 0.48070(7) 0.66586(17) 0.0161(2) Uani 1 1 d . . . . . C3 C 0.65109(12) 0.75269(6) 0.70074(17) 0.0165(2) Uani 1 1 d . . . . . C4 C 0.77107(12) 0.84771(7) 0.65698(17) 0.0186(2) Uani 1 1 d . . . . . N1 N 0.73930(10) 0.27759(6) 0.58290(16) 0.0216(2) Uani 1 1 d . . . . . N2 N 0.82883(10) 0.41162(6) 0.56244(16) 0.0202(2) Uani 1 1 d . . . . . N3 N 0.63695(10) 0.40298(6) 0.67017(15) 0.0171(2) Uani 1 1 d . . . . . N4 N 0.78792(9) 0.48729(6) 0.60330(15) 0.0186(2) Uani 1 1 d . . . . . H4 H 0.829026 0.533422 0.590774 0.022 Uiso 1 1 calc R U . . . N5 N 0.60625(10) 0.54697(6) 0.71442(15) 0.0184(2) Uani 1 1 d . . . . . H5 H 0.533804 0.541804 0.760096 0.022 Uiso 1 1 calc R U . . . N6 N 0.65792(10) 0.61948(6) 0.68701(14) 0.0174(2) Uani 1 1 d . . . . . N7 N 0.58976(10) 0.67874(6) 0.72740(15) 0.0183(2) Uani 1 1 d . . . . . N8 N 0.59184(10) 0.82414(6) 0.72312(15) 0.0182(2) Uani 1 1 d . . . . . H8 H 0.513908 0.829049 0.751894 0.022 Uiso 1 1 calc R U . . . N9 N 0.66932(10) 0.88712(6) 0.69501(15) 0.0199(2) Uani 1 1 d . . . . . N10 N 0.76790(10) 0.76558(6) 0.65723(14) 0.0176(2) Uani 1 1 d . . . . . N11 N 0.88133(10) 0.89362(6) 0.61330(17) 0.0240(2) Uani 1 1 d . . . . . O1 O 0.64701(10) 0.23915(5) 0.62353(16) 0.0297(2) Uani 1 1 d . . . . . O2 O 0.83147(10) 0.24764(5) 0.52497(17) 0.0339(3) Uani 1 1 d . . . A 1 O3 O 0.87349(10) 0.96869(6) 0.61812(18) 0.0396(3) Uani 1 1 d . . . . . O4 O 0.97216(10) 0.85482(6) 0.57620(16) 0.0338(2) Uani 1 1 d . . . B 1 O5 O 0.38511(10) 0.56033(5) 0.85590(17) 0.0323(2) Uani 1 1 d . . . . . O6 O 0.92472(9) 0.62309(5) 0.56473(15) 0.0261(2) Uani 1 1 d . . . . . H5A H 0.351390 0.606886 0.869682 0.039 Uiso 1 1 d R U . . . H6A H 0.899400 0.668746 0.603002 0.039 Uiso 1 1 d R U . . . H5B H 0.325650 0.523486 0.842952 0.039 Uiso 1 1 d R U . . . H6B H 1.003810 0.623206 0.551642 0.039 Uiso 1 1 d R U . . . 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 0.0163(5) 0.0142(5) 0.0220(6) -0.0009(4) 0.0066(4) 0.0013(4) C2 0.0162(5) 0.0146(5) 0.0178(5) 0.0002(4) 0.0045(4) 0.0011(4) C3 0.0193(6) 0.0145(5) 0.0159(5) -0.0005(4) 0.0042(4) 0.0021(4) C4 0.0194(6) 0.0162(5) 0.0199(6) -0.0004(4) 0.0035(5) -0.0005(4) N1 0.0211(5) 0.0153(5) 0.0301(6) -0.0018(4) 0.0089(4) 0.0012(4) N2 0.0187(5) 0.0147(4) 0.0290(6) -0.0004(4) 0.0089(4) 0.0013(4) N3 0.0170(5) 0.0132(4) 0.0224(5) -0.0006(4) 0.0074(4) 0.0001(4) N4 0.0180(5) 0.0125(4) 0.0273(5) -0.0002(4) 0.0093(4) -0.0002(4) N5 0.0183(5) 0.0130(4) 0.0265(5) -0.0005(4) 0.0106(4) -0.0002(4) N6 0.0196(5) 0.0137(4) 0.0194(5) -0.0002(3) 0.0049(4) 0.0006(4) N7 0.0202(5) 0.0147(5) 0.0213(5) -0.0005(4) 0.0070(4) 0.0014(4) N8 0.0174(5) 0.0142(4) 0.0239(5) -0.0008(4) 0.0065(4) 0.0012(3) N9 0.0205(5) 0.0147(5) 0.0247(5) -0.0003(4) 0.0046(4) -0.0009(4) N10 0.0187(5) 0.0158(4) 0.0189(5) -0.0005(4) 0.0054(4) 0.0003(4) N11 0.0226(5) 0.0199(5) 0.0300(6) 0.0002(4) 0.0068(5) -0.0021(4) O1 0.0289(5) 0.0161(4) 0.0480(6) -0.0004(4) 0.0168(4) -0.0044(3) O2 0.0292(5) 0.0224(5) 0.0554(7) -0.0077(4) 0.0211(5) 0.0052(4) O3 0.0377(6) 0.0179(4) 0.0677(8) 0.0039(5) 0.0213(6) -0.0042(4) O4 0.0254(5) 0.0320(5) 0.0481(6) -0.0050(4) 0.0172(5) -0.0009(4) O5 0.0288(5) 0.0161(4) 0.0570(7) -0.0043(4) 0.0208(5) -0.0037(3) O6 0.0191(4) 0.0188(4) 0.0437(6) -0.0014(4) 0.0141(4) -0.0012(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 N2 C1 N3 118.20(10) . . ? N2 C1 N1 120.50(10) . . ? N3 C1 N1 121.30(10) . . ? N3 C2 N4 111.64(10) . . ? N3 C2 N5 124.94(10) . . ? N4 C2 N5 123.40(10) . . ? N10 C3 N8 110.69(10) . . ? N10 C3 N7 129.23(10) . . ? N8 C3 N7 120.07(10) . . ? N9 C4 N10 117.91(11) . . ? N9 C4 N11 119.69(10) . . ? N10 C4 N11 122.39(10) . . ? O2 N1 O1 125.34(10) . . ? O2 N1 C1 118.24(10) . . ? O1 N1 C1 116.42(10) . . ? C1 N2 N4 101.18(9) . . ? C2 N3 C1 99.80(9) . . ? C2 N4 N2 109.17(9) . . ? N6 N5 C2 114.81(9) . . ? N7 N6 N5 112.77(10) . . ? N6 N7 C3 109.81(10) . . ? C3 N8 N9 109.99(10) . . ? C4 N9 N8 100.91(9) . . ? C3 N10 C4 100.51(9) . . ? O4 N11 O3 125.93(11) . . ? O4 N11 C4 117.46(10) . . ? O3 N11 C4 116.61(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 N2 1.3071(15) . ? C1 N3 1.3473(14) . ? C1 N1 1.4510(14) . ? C2 N3 1.3314(14) . ? C2 N4 1.3414(14) . ? C2 N5 1.3752(14) . ? C3 N10 1.3314(16) . ? C3 N8 1.3442(14) . ? C3 N7 1.3964(14) . ? C4 N9 1.3138(15) . ? C4 N10 1.3415(14) . ? C4 N11 1.4562(15) . ? N1 O2 1.2166(14) . ? N1 O1 1.2294(14) . ? N2 N4 1.3551(13) . ? N5 N6 1.3305(13) . ? N6 N7 1.2650(13) . ? N8 N9 1.3469(13) . ? N11 O4 1.2107(14) . ? N11 O3 1.2294(14) . ?