#------------------------------------------------------------------------------ #$Date: 2021-11-03 03:34:01 +0200 (Wed, 03 Nov 2021) $ #$Revision: 270221 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061034.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_7061034 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 H4 N12 O2' _chemical_formula_sum 'C5 H4 N12 O2' _chemical_formula_weight 264.20 _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-2018/3 _audit_update_record ; 2021-10-02 deposited with the CCDC. 2021-10-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.273(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.252(2) _cell_length_b 4.7966(8) _cell_length_c 17.536(3) _cell_measurement_reflns_used 3864 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.73 _cell_measurement_theta_min 3.19 _cell_volume 1075.3(3) _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 296(2) _diffrn_detector_area_resol_mean 10.42 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker D8 QUEST PHOTON 100' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_unetI/netI 0.0397 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9641 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.644 _diffrn_reflns_theta_min 3.187 _diffrn_source.source 'Ius 2.0' _diffrn_source.type microfocus _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5911 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.632 _exptl_crystal_description plate _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.010 _refine_diff_density_max 0.161 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.032 _refine_ls_extinction_coef 0.022(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2481 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0407 _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^)+(0.0437P)^2^+0.1642P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0884 _refine_ls_wR_factor_ref 0.1007 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1624 _reflns_number_total 2481 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04188f2.cif _cod_data_source_block Wq190614_a _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7061034 _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 0.971 _shelx_estimated_absorpt_t_max 0.999 _shelx_res_file ; TITL Wq190614_a.res in P2(1)/n Wq190614_a.res created by SHELXL-2018/3 at 10:49:10 on 17-Sep-2021 CELL 0.71073 13.2524 4.7966 17.5360 90.000 105.273 90.000 ZERR 4.00 0.0022 0.0008 0.0028 0.000 0.005 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H N O UNIT 20 16 48 8 omit 0 0 4 omit 0 0 2 omit 1 0 1 L.S. 10 ACTA BOND $H FMAP 2 PLAN -5 HTAB N6 N9_$2 HTAB N6 O2_$2 EQIV $2 -x+1/2, y+1/2, -z+1/2 HTAB N7 N2_$1 EQIV $1 -x+1, -y+1, -z+1 size 0.22 0.18 0.01 CONF TEMP 23.000 WGHT 0.043700 0.164200 EXTI 0.022474 FVAR 1.06677 C1 1 0.612855 0.354395 0.284550 11.00000 0.03534 0.06230 = 0.04290 0.00767 0.01056 -0.00678 C2 1 0.570385 0.488809 0.342036 11.00000 0.03571 0.05527 = 0.03708 0.00374 0.00702 -0.01329 C3 1 0.460621 0.808167 0.392050 11.00000 0.05685 0.05365 = 0.04578 -0.00566 0.01506 -0.00945 AFIX 23 H3A 2 0.423499 0.980688 0.374637 11.00000 -1.20000 H3B 2 0.518916 0.850624 0.437101 11.00000 -1.20000 AFIX 0 C4 1 0.289037 0.602238 0.372437 11.00000 0.05216 0.04413 = 0.03740 -0.00724 0.01798 -0.00015 C5 1 0.211597 0.417888 0.385318 11.00000 0.05065 0.04707 = 0.04021 -0.00808 0.01684 -0.00063 N1 3 0.680459 0.166677 0.317354 11.00000 0.04970 0.07791 = 0.05217 0.01197 0.01359 0.00385 N2 3 0.612795 0.377142 0.410693 11.00000 0.04840 0.06730 = 0.04209 0.00415 0.00740 -0.00606 N3 3 0.582222 0.423427 0.204499 11.00000 0.05294 0.08364 = 0.04225 0.00788 0.02031 0.01209 N4 3 0.616912 0.265115 0.161046 11.00000 0.06279 0.09272 = 0.04826 0.01036 0.02055 0.01596 N5 3 0.640979 0.143067 0.114840 11.00000 0.11958 0.12891 = 0.06272 0.00285 0.03803 0.04484 N6 3 0.500252 0.698822 0.329227 11.00000 0.04818 0.06438 = 0.03716 0.00494 0.01007 -0.00257 H6 2 0.468248 0.732730 0.282728 11.00000 -1.20000 N7 3 0.390898 0.615468 0.416373 11.00000 0.05301 0.06187 = 0.03931 -0.00118 0.01703 -0.00685 H7 2 0.396887 0.593694 0.463347 11.00000 -1.20000 N8 3 0.248822 0.753032 0.310385 11.00000 0.06196 0.05421 = 0.05037 -0.00058 0.01275 -0.00228 N9 3 0.123885 0.454305 0.332002 11.00000 0.05558 0.05985 = 0.05317 -0.00376 0.01411 -0.00199 N10 3 0.232047 0.228385 0.447628 11.00000 0.05650 0.06343 = 0.05123 0.00188 0.01719 -0.01458 AFIX 2 N11 3 0.156431 0.079965 0.452575 11.00000 0.06470 0.06237 = 0.04693 -0.00578 0.01963 -0.00794 AFIX 0 N12 3 0.097784 -0.069250 0.464942 11.00000 0.08325 0.08893 = 0.07915 -0.00093 0.03045 -0.02732 O1 4 0.683137 0.175039 0.396791 11.00000 0.05682 0.08182 = 0.05038 0.01621 0.00689 0.00661 O2 4 0.144702 0.665662 0.283809 11.00000 0.06160 0.06519 = 0.05664 0.00226 0.00599 0.00340 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM Wq190614_a.res in P2(1)/n REM wR2 = 0.1007, GooF = S = 1.013, Restrained GooF = 1.013 for all data REM R1 = 0.0407 for 1624 Fo > 4sig(Fo) and 0.0789 for all 2481 data REM 173 parameters refined using 0 restraints END WGHT 0.0433 0.1659 REM Highest difference peak 0.161, deepest hole -0.131, 1-sigma level 0.032 Q1 1 0.6223 0.4419 0.4585 11.00000 0.05 0.16 Q2 1 0.6158 0.4375 0.2594 11.00000 0.05 0.13 Q3 1 0.2167 0.3209 0.4061 11.00000 0.05 0.12 Q4 1 0.5760 0.3307 0.2447 11.00000 0.05 0.12 Q5 1 0.5810 -0.0008 0.1178 11.00000 0.05 0.12 ; _shelx_res_checksum 34360 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 0.61285(11) 0.3544(4) 0.28455(8) 0.0468(4) Uani 1 1 d . . . . . C2 C 0.57039(11) 0.4888(3) 0.34204(8) 0.0432(4) Uani 1 1 d . . . . . C3 C 0.46062(13) 0.8082(3) 0.39205(9) 0.0518(4) Uani 1 1 d . . . . . H3A H 0.423499 0.980688 0.374637 0.062 Uiso 1 1 calc R U . . . H3B H 0.518916 0.850624 0.437101 0.062 Uiso 1 1 calc R U . . . C4 C 0.28904(12) 0.6022(3) 0.37244(8) 0.0434(4) Uani 1 1 d . . . . . C5 C 0.21160(12) 0.4179(3) 0.38532(8) 0.0451(4) Uani 1 1 d . . . . . N1 N 0.68046(11) 0.1667(3) 0.31735(8) 0.0599(4) Uani 1 1 d . . . . . N2 N 0.61280(10) 0.3771(3) 0.41069(7) 0.0534(4) Uani 1 1 d . . . . . N3 N 0.58222(10) 0.4234(3) 0.20450(7) 0.0581(4) Uani 1 1 d . . . . . N4 N 0.61691(12) 0.2651(4) 0.16105(9) 0.0668(4) Uani 1 1 d . . . . . N5 N 0.64098(17) 0.1431(5) 0.11484(10) 0.1011(7) Uani 1 1 d . . . . . N6 N 0.50025(10) 0.6988(3) 0.32923(7) 0.0501(4) Uani 1 1 d . . . . . H6 H 0.4682(13) 0.733(4) 0.2827(10) 0.060 Uiso 1 1 d . U . . . N7 N 0.39090(10) 0.6155(3) 0.41637(7) 0.0505(4) Uani 1 1 d . . . . . H7 H 0.3969(14) 0.594(4) 0.4633(11) 0.061 Uiso 1 1 d . U . . . N8 N 0.24882(11) 0.7530(3) 0.31038(7) 0.0559(4) Uani 1 1 d . . . . . N9 N 0.12388(11) 0.4543(3) 0.33200(8) 0.0562(4) Uani 1 1 d . . . . . N10 N 0.23205(11) 0.2284(3) 0.44763(7) 0.0565(4) Uani 1 1 d . . . . . N11 N 0.15643(12) 0.0800(3) 0.45258(7) 0.057 Uani 1 1 d . . . . . N12 N 0.09778(14) -0.0693(4) 0.46494(9) 0.0821(5) Uani 1 1 d . . . . . O1 O 0.68314(9) 0.1750(3) 0.39679(6) 0.0644(4) Uani 1 1 d . . . . . O2 O 0.14470(9) 0.6657(3) 0.28381(6) 0.0630(3) 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 0.0353(8) 0.0623(10) 0.0429(8) 0.0077(7) 0.0106(6) -0.0068(8) C2 0.0357(8) 0.0553(9) 0.0371(8) 0.0037(7) 0.0070(6) -0.0133(8) C3 0.0569(10) 0.0536(10) 0.0458(8) -0.0057(7) 0.0151(7) -0.0095(9) C4 0.0522(9) 0.0441(8) 0.0374(8) -0.0072(6) 0.0180(7) -0.0001(8) C5 0.0506(9) 0.0471(9) 0.0402(8) -0.0081(7) 0.0168(7) -0.0006(8) N1 0.0497(8) 0.0779(10) 0.0522(8) 0.0120(7) 0.0136(6) 0.0038(8) N2 0.0484(8) 0.0673(9) 0.0421(7) 0.0041(6) 0.0074(6) -0.0061(7) N3 0.0529(8) 0.0836(11) 0.0423(7) 0.0079(7) 0.0203(6) 0.0121(8) N4 0.0628(10) 0.0927(12) 0.0483(8) 0.0104(8) 0.0206(7) 0.0160(9) N5 0.1196(16) 0.1289(17) 0.0627(11) 0.0029(11) 0.0380(11) 0.0448(14) N6 0.0482(8) 0.0644(9) 0.0372(7) 0.0049(6) 0.0101(6) -0.0026(7) N7 0.0530(8) 0.0619(9) 0.0393(7) -0.0012(6) 0.0170(6) -0.0068(7) N8 0.0620(9) 0.0542(8) 0.0504(8) -0.0006(6) 0.0128(6) -0.0023(7) N9 0.0556(8) 0.0599(9) 0.0532(8) -0.0038(7) 0.0141(6) -0.0020(7) N10 0.0565(9) 0.0634(9) 0.0512(8) 0.0019(7) 0.0172(6) -0.0146(7) N11 0.065 0.062 0.047 -0.006 0.020 -0.008 N12 0.0832(12) 0.0889(12) 0.0791(11) -0.0009(9) 0.0304(9) -0.0273(10) O1 0.0568(7) 0.0818(8) 0.0504(7) 0.0162(6) 0.0069(5) 0.0066(7) O2 0.0616(7) 0.0652(8) 0.0566(7) 0.0023(6) 0.0060(5) 0.0034(6) 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 N1 C1 N3 126.65(15) . . ? N1 C1 C2 110.81(13) . . ? N3 C1 C2 122.54(14) . . ? N2 C2 N6 124.88(14) . . ? N2 C2 C1 108.18(14) . . ? N6 C2 C1 126.93(13) . . ? N6 C3 N7 112.51(13) . . ? N6 C3 H3A 109.1 . . ? N7 C3 H3A 109.1 . . ? N6 C3 H3B 109.1 . . ? N7 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? N8 C4 N7 124.92(14) . . ? N8 C4 C5 109.06(14) . . ? N7 C4 C5 125.99(14) . . ? N9 C5 N10 127.29(15) . . ? N9 C5 C4 110.49(14) . . ? N10 C5 C4 122.22(14) . . ? C1 N1 O1 104.98(13) . . ? C2 N2 O1 105.48(12) . . ? N4 N3 C1 114.48(14) . . ? N5 N4 N3 171.44(19) . . ? C2 N6 C3 121.29(13) . . ? C2 N6 H6 117.5(12) . . ? C3 N6 H6 119.1(12) . . ? C4 N7 C3 118.37(13) . . ? C4 N7 H7 112.5(12) . . ? C3 N7 H7 118.7(13) . . ? C4 N8 O2 105.27(13) . . ? C5 N9 O2 104.60(13) . . ? N11 N10 C5 115.61(13) . . ? N12 N11 N10 170.96(18) . . ? N1 O1 N2 110.55(11) . . ? N9 O2 N8 110.57(11) . . ? 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 N1 1.293(2) . ? C1 N3 1.3946(18) . ? C1 C2 1.431(2) . ? C2 N2 1.3022(18) . ? C2 N6 1.349(2) . ? C3 N6 1.4386(19) . ? C3 N7 1.448(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N8 1.2984(19) . ? C4 N7 1.3682(19) . ? C4 C5 1.417(2) . ? C5 N9 1.297(2) . ? C5 N10 1.392(2) . ? N1 O1 1.3847(17) . ? N2 O1 1.4099(18) . ? N3 N4 1.246(2) . ? N4 N5 1.112(2) . ? N6 H6 0.830(17) . ? N7 H7 0.813(17) . ? N8 O2 1.3993(17) . ? N9 O2 1.3932(18) . ? N10 N11 1.251(2) . ? N11 N12 1.1190(19) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N6 H6 N9 0.830(17) 2.318(18) 3.1227(19) 163.4(16) 2 yes N6 H6 O2 0.830(17) 2.645(18) 3.2600(19) 132.1(15) 2 yes N7 H7 N2 0.813(17) 2.250(18) 3.0460(18) 166.1(17) 3_666 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -0.62(18) . . . . ? N3 C1 C2 N2 179.02(14) . . . . ? N1 C1 C2 N6 178.12(14) . . . . ? N3 C1 C2 N6 -2.2(2) . . . . ? N8 C4 C5 N9 -0.26(17) . . . . ? N7 C4 C5 N9 -178.40(14) . . . . ? N8 C4 C5 N10 179.60(14) . . . . ? N7 C4 C5 N10 1.5(2) . . . . ? N3 C1 N1 O1 -179.52(15) . . . . ? C2 C1 N1 O1 0.10(17) . . . . ? N6 C2 N2 O1 -177.95(13) . . . . ? C1 C2 N2 O1 0.82(15) . . . . ? N1 C1 N3 N4 7.8(2) . . . . ? C2 C1 N3 N4 -171.75(14) . . . . ? N2 C2 N6 C3 -4.0(2) . . . . ? C1 C2 N6 C3 177.46(14) . . . . ? N7 C3 N6 C2 -70.82(18) . . . . ? N8 C4 N7 C3 -0.9(2) . . . . ? C5 C4 N7 C3 176.92(13) . . . . ? N6 C3 N7 C4 -81.16(17) . . . . ? N7 C4 N8 O2 178.59(13) . . . . ? C5 C4 N8 O2 0.43(15) . . . . ? N10 C5 N9 O2 -179.89(14) . . . . ? C4 C5 N9 O2 -0.04(16) . . . . ? N9 C5 N10 N11 -0.8(2) . . . . ? C4 C5 N10 N11 179.34(13) . . . . ? C1 N1 O1 N2 0.42(16) . . . . ? C2 N2 O1 N1 -0.80(15) . . . . ? C5 N9 O2 N8 0.31(16) . . . . ? C4 N8 O2 N9 -0.47(15) . . . . ?