#------------------------------------------------------------------------------ #$Date: 2021-05-15 07:01:30 +0300 (Sat, 15 May 2021) $ #$Revision: 265240 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/28/7242871.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_7242871 loop_ _publ_author_name 'Wozniak, Dominique R.' 'Zeller, Matthias' 'Byrd, Edward F. C.' 'Piercey, Davin G.' _publ_section_title ; 3-Methyl-1,2,3-triazolium-1N-dinitromethylylide and the strategy of zwitterionic dinitromethyl groups in energetic materials design ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 17710 _journal_page_last 17714 _journal_paper_doi 10.1039/D1RA00953B _journal_volume 11 _journal_year 2021 _chemical_formula_sum 'C4 H5 N5 O4' _chemical_formula_weight 187.13 _space_group_crystal_system orthorhombic _space_group_IT_number 64 _space_group_name_Hall '-C 2ac 2' _space_group_name_H-M_alt 'C m c e' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-12-09 deposited with the CCDC. 2021-04-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 7.7002(7) _cell_length_b 14.3978(16) _cell_length_c 12.7602(11) _cell_measurement_reflns_used 3719 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 79.8878 _cell_measurement_theta_min 6.1494 _cell_volume 1414.7(2) _computing_cell_refinement 'SAINT V8.40A (Bruker, 2019)' _computing_data_collection 'Apex3 v2019.1-0 (Bruker, 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker, 2019)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2015, 2018), SHELXLE Rev1143 (H\"ubschle et al., 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 7.4074 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measurement_device_type ; Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and photon counting pixel array detector ; _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator 'laterally graded multilayer (Goebel) mirror' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_unetI/netI 0.0376 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.970 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5056 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.970 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 79.922 _diffrn_reflns_theta_min 6.147 _diffrn_source 'I-mu-S microsource X-ray tube' _diffrn_source_current '1.0 mA' _diffrn_source_voltage '50 kV' _exptl_absorpt_coefficient_mu 1.382 _exptl_absorpt_correction_T_max 0.7543 _exptl_absorpt_correction_T_min 0.6126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.757 _exptl_crystal_description plate _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.321 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.063 _refine_ls_extinction_coef 0.0052(11) _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 1.160 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 72 _refine_ls_number_reflns 812 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.160 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0461 _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^)+(0.0842P)^2^+0.8362P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1406 _refine_ls_wR_factor_ref 0.1427 _reflns_Friedel_coverage 0.000 _reflns_number_gt 741 _reflns_number_total 812 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra00953b2.cif _cod_data_source_block L2DW22G_0m _cod_original_sg_symbol_Hall '-C 2bc 2' _cod_original_sg_symbol_H-M 'C m c a' _cod_database_code 7242871 _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 0.809 _shelx_estimated_absorpt_t_max 0.973 _shelx_res_file ; TITL L2DW22G_0m in Cmca L2DW22G_0m.res created by SHELXL-2018/3 at 13:00:24 on 12-Sep-2020 CELL 1.54178 7.70020 14.39779 12.76020 90.0000 90.0000 90.0000 ZERR 8.00 0.00070 0.00157 0.00110 0.0000 0.0000 0.0000 LATT 7 SYMM -X, 0.5-Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM X, -Y, -Z SFAC C H N O UNIT 32 40 40 32 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -123.150 SIZE 0.02 0.15 0.16 L.S. 4 BOND $H ACTA CONF FMAP 2 PLAN 20 WGHT 0.084200 0.836200 EXTI 0.005207 FVAR 0.72338 C1 1 0.000000 0.297435 -0.184272 10.50000 0.03133 0.02419 = 0.02611 -0.00221 0.00000 0.00000 AFIX 43 H1 2 0.000000 0.232183 -0.173226 10.50000 -1.20000 AFIX 0 C2 1 0.000000 0.343189 -0.277675 10.50000 0.03221 0.02851 = 0.02215 -0.00313 0.00000 0.00000 AFIX 43 H2 2 0.000000 0.316490 -0.345758 10.50000 -1.20000 AFIX 0 C3 1 0.000000 0.512967 -0.326936 10.50000 0.05123 0.02771 = 0.02750 0.00606 0.00000 0.00000 AFIX 137 H3A 2 0.052097 0.493417 -0.393446 10.50000 -1.50000 H3B 2 0.067562 0.564336 -0.297327 10.50000 -1.50000 H3C 2 -0.119658 0.533459 -0.339175 10.50000 -1.50000 AFIX 0 C4 1 0.000000 0.354383 -0.001235 10.50000 0.02297 0.03258 = 0.02065 0.00169 0.00000 0.00000 N1 3 0.000000 0.364907 -0.110741 10.50000 0.02846 0.02623 = 0.02059 0.00010 0.00000 0.00000 N2 3 0.000000 0.450102 -0.151849 10.50000 0.04117 0.02575 = 0.02198 0.00028 0.00000 0.00000 N3 3 0.000000 0.434524 -0.253250 10.50000 0.02973 0.02621 = 0.02017 0.00128 0.00000 0.00000 N4 3 0.159576 0.350844 0.048069 11.00000 0.02880 0.02598 = 0.02387 -0.00030 0.00053 -0.00069 O1 4 0.290811 0.359789 -0.009248 11.00000 0.02553 0.04722 = 0.03272 -0.00256 0.00627 -0.00510 O2 4 0.171408 0.339252 0.143996 11.00000 0.03367 0.03808 = 0.02229 0.00285 -0.00483 -0.00080 HKLF 4 REM L2DW22G_0m in Cmca REM wR2 = 0.1427, GooF = S = 1.160, Restrained GooF = 1.160 for all data REM R1 = 0.0461 for 741 Fo > 4sig(Fo) and 0.0483 for all 812 data REM 72 parameters refined using 0 restraints END WGHT 0.0842 0.8368 REM Highest difference peak 0.321, deepest hole -0.249, 1-sigma level 0.063 Q1 1 0.0000 0.2448 -0.1236 10.50000 0.05 0.28 Q2 1 0.0000 0.4552 -0.4965 10.50000 0.05 0.24 Q3 1 0.0000 0.3140 -0.2324 10.50000 0.05 0.22 Q4 1 0.0000 0.3329 -0.3729 10.50000 0.05 0.22 Q5 1 0.0000 0.3614 0.1071 10.50000 0.05 0.21 Q6 1 0.2858 0.3503 -0.0962 11.00000 0.05 0.19 Q7 1 0.1502 0.3411 -0.0570 11.00000 0.05 0.19 Q8 1 0.1651 0.4325 0.1103 11.00000 0.05 0.18 Q9 1 0.3321 0.3391 0.1495 11.00000 0.05 0.18 Q10 1 0.0000 0.3509 0.1520 10.50000 0.05 0.18 Q11 1 -0.1584 0.5364 -0.3042 11.00000 0.05 0.17 Q12 1 0.1737 0.4292 0.0027 11.00000 0.05 0.17 Q13 1 0.0000 0.2745 -0.1807 10.50000 0.05 0.17 Q14 1 0.1396 0.4952 -0.3747 11.00000 0.05 0.17 Q15 1 0.1656 0.4235 0.1949 11.00000 0.05 0.17 Q16 1 0.1445 0.2509 0.1818 11.00000 0.05 0.17 Q17 1 0.0000 0.2477 -0.0180 10.50000 0.05 0.17 Q18 1 0.1686 0.2832 -0.0159 11.00000 0.05 0.16 Q19 1 0.0000 0.3076 0.1822 10.50000 0.05 0.16 Q20 1 0.0680 0.2320 -0.1449 11.00000 0.05 0.16 ; _shelx_res_checksum 21122 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' 'x+1/2, -y, z-1/2' '-x+1/2, y+1/2, z' 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 0.000000 0.29744(15) -0.18427(17) 0.0272(6) Uani 1 2 d S T P . . H1 H 0.000000 0.232183 -0.173226 0.033 Uiso 1 2 calc R U P . . C2 C 0.000000 0.34319(15) -0.27768(18) 0.0276(6) Uani 1 2 d S T P . . H2 H 0.000000 0.316490 -0.345758 0.033 Uiso 1 2 calc R U P . . C3 C 0.000000 0.51297(16) -0.32694(19) 0.0355(6) Uani 1 2 d S T P . . H3A H 0.052097 0.493417 -0.393446 0.053 Uiso 0.5 1 calc R U P . . H3B H 0.067562 0.564336 -0.297327 0.053 Uiso 0.5 1 calc R U P . . H3C H -0.119658 0.533459 -0.339175 0.053 Uiso 0.5 1 calc R U P . . C4 C 0.000000 0.35438(15) -0.00123(18) 0.0254(5) Uani 1 2 d S T P . . N1 N 0.000000 0.36491(13) -0.11074(14) 0.0251(5) Uani 1 2 d S T P . . N2 N 0.000000 0.45010(13) -0.15185(15) 0.0296(5) Uani 1 2 d S T P . . N3 N 0.000000 0.43452(13) -0.25325(14) 0.0254(5) Uani 1 2 d S T P . . N4 N 0.15958(18) 0.35084(9) 0.04807(11) 0.0262(4) Uani 1 1 d . . . . . O1 O 0.29081(16) 0.35979(9) -0.00925(10) 0.0352(4) Uani 1 1 d . . . . . O2 O 0.17141(17) 0.33925(8) 0.14400(9) 0.0313(4) 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 0.0313(12) 0.0242(10) 0.0261(11) -0.0022(8) 0.000 0.000 C2 0.0322(12) 0.0285(11) 0.0222(11) -0.0031(7) 0.000 0.000 C3 0.0512(16) 0.0277(11) 0.0275(11) 0.0061(9) 0.000 0.000 C4 0.0230(12) 0.0326(11) 0.0207(11) 0.0017(7) 0.000 0.000 N1 0.0285(10) 0.0262(9) 0.0206(10) 0.0001(6) 0.000 0.000 N2 0.0412(12) 0.0257(9) 0.0220(10) 0.0003(7) 0.000 0.000 N3 0.0297(10) 0.0262(9) 0.0202(9) 0.0013(6) 0.000 0.000 N4 0.0288(8) 0.0260(7) 0.0239(8) -0.0003(4) 0.0005(5) -0.0007(5) O1 0.0255(8) 0.0472(8) 0.0327(7) -0.0026(5) 0.0063(5) -0.0051(5) O2 0.0337(7) 0.0381(7) 0.0223(7) 0.0028(4) -0.0048(4) -0.0008(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C2 105.07(19) . . ? N1 C1 H1 127.5 . . ? C2 C1 H1 127.5 . . ? N3 C2 C1 105.60(19) . . ? N3 C2 H2 127.2 . . ? C1 C2 H2 127.2 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N3 C3 H3A 109.5(4) . 12 ? H3A C3 H3A 48.3 . 12 ? H3B C3 H3A 140.2 . 12 ? H3C C3 H3A 64.1 . 12 ? N3 C3 H3B 109.5(4) . 12 ? H3A C3 H3B 140.2 . 12 ? H3B C3 H3B 64.1 . 12 ? H3C C3 H3B 48.3 . 12 ? H3A C3 H3B 109.5 12 12 ? N3 C3 H3C 109.47(7) . 12 ? H3A C3 H3C 64.1 . 12 ? H3B C3 H3C 48.3 . 12 ? H3C C3 H3C 140.2 . 12 ? H3A C3 H3C 109.5 12 12 ? H3B C3 H3C 109.5 12 12 ? N4 C4 N4 125.6(2) 12 . ? N4 C4 N1 117.18(10) 12 . ? N4 C4 N1 117.18(10) . . ? N2 N1 C1 112.84(18) . . ? N2 N1 C4 119.34(17) . . ? C1 N1 C4 127.82(19) . . ? N3 N2 N1 103.32(16) . . ? N2 N3 C2 113.17(18) . . ? N2 N3 C3 119.94(18) . . ? C2 N3 C3 126.89(19) . . ? O2 N4 O1 122.06(14) . . ? O2 N4 C4 121.36(14) . . ? O1 N4 C4 116.58(14) . . ? 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 1.351(3) . ? C1 C2 1.362(3) . ? C1 H1 0.9500 . ? C2 N3 1.351(3) . ? C2 H2 0.9500 . ? C3 N3 1.470(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C3 H3A 0.980(16) 12 ? C3 H3B 0.98(2) 12 ? C3 H3C 0.980(3) 12 ? C4 N4 1.3814(17) 12 ? C4 N4 1.3814(17) . ? C4 N1 1.406(3) . ? N1 N2 1.334(2) . ? N2 N3 1.313(3) . ? N4 O2 1.2387(18) . ? N4 O1 1.2541(18) . ? 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 N3 0.000(0) . . . . ? C2 C1 N1 N2 0.000(0) . . . . ? C2 C1 N1 C4 180.000(0) . . . . ? N4 C4 N1 N2 89.20(16) 12 . . . ? N4 C4 N1 N2 -89.20(16) . . . . ? N4 C4 N1 C1 -90.80(16) 12 . . . ? N4 C4 N1 C1 90.80(16) . . . . ? C1 N1 N2 N3 0.000(0) . . . . ? C4 N1 N2 N3 180.000(0) . . . . ? N1 N2 N3 C2 0.000(0) . . . . ? N1 N2 N3 C3 180.000(0) . . . . ? C1 C2 N3 N2 0.000(0) . . . . ? C1 C2 N3 C3 180.000(0) . . . . ? N4 C4 N4 O2 3.7(3) 12 . . . ? N1 C4 N4 O2 -178.09(15) . . . . ? N4 C4 N4 O1 -176.46(14) 12 . . . ? N1 C4 N4 O1 1.8(2) . . . . ?