#------------------------------------------------------------------------------ #$Date: 2019-11-07 21:36:09 +0200 (Thu, 07 Nov 2019) $ #$Revision: 223555 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233848.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_7233848 loop_ _publ_author_name 'Wang, Yanna' 'Yang, Xiaoming' 'Zhang, Weijing' 'Li, Haibo' 'Li, Zhimin' 'Wang, Lin' 'Zhang, Tonglai' _publ_section_title ; Energetic transition metal salts of 5,5′-dinitramino-3,3′-methylene-1H-1,2,4-bistriazole: syntheses, structures and properties ; _journal_issue 42 _journal_name_full CrystEngComm _journal_page_first 6452 _journal_paper_doi 10.1039/C9CE01158G _journal_volume 21 _journal_year 2019 _chemical_formula_moiety 'C5 H12 N10 Ni O8, 2(H2 O)' _chemical_formula_sum 'C5 H16 N10 Ni O10' _chemical_formula_weight 434.99 _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_space_group_name_H-M 'P n m a' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2019-09-06 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-09-06 deposited with the CCDC. 2019-09-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.6991(19) _cell_length_b 14.573(3) _cell_length_c 11.082(2) _cell_measurement_reflns_used 5018 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 27.4816 _cell_measurement_theta_min 1.3974 _cell_volume 1566.4(5) _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 153.15 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type AFC10\SATURN724+ _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 0.0374 _diffrn_reflns_av_unetI/netI 0.0333 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6025 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.473 _diffrn_reflns_theta_min 2.795 _exptl_absorpt_coefficient_mu 1.317 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.845 _exptl_crystal_description block _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.613 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 134 _refine_ls_number_reflns 1846 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.103 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0400 _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^)+(0.0351P)^2^+2.3571P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.0940 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1739 _reflns_number_total 1846 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL bwn18353-a in Pnma bwn18353-a.res created by SHELXL-2018/3 at 16:14:15 on 06-Sep-2019 CELL 0.71073 9.6991 14.5728 11.0816 90 90 90 ZERR 4 0.0019 0.0029 0.0022 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,-Z SYMM 0.5+X,0.5-Y,0.5-Z SFAC C H N Ni O UNIT 20 64 40 4 40 SIMU 0.01 0.01 1.7 O6A O6 ISOR 0.01 0.02 O6A O6 L.S. 4 PLAN 5 SIZE 0.13 0.12 0.1 TEMP -120 BOND $H CONF fmap 2 acta OMIT 3 5 1 OMIT 3 5 2 OMIT 1 0 1 OMIT 2 1 0 REM REM REM WGHT 0.035100 2.357100 FVAR 0.48375 0.52964 NI1 4 0.238802 0.750000 0.894227 10.50000 0.01478 0.01186 = 0.01369 0.00000 0.00073 0.00000 O3 5 0.184890 0.750000 0.710367 10.50000 0.03601 0.02422 = 0.01450 0.00000 -0.00218 0.00000 AFIX 3 0.8400 H3 2 0.205820 0.703960 0.668597 11.00000 -1.20000 AFIX 0 O4 5 0.300036 0.750000 1.069603 10.50000 0.03503 0.01269 = 0.01333 0.00000 -0.00435 0.00000 AFIX 3 0.8400 H4 2 0.295316 0.702510 1.112383 11.00000 -1.20000 AFIX 0 N4 3 -0.063662 0.540824 0.885168 11.00000 0.01600 0.01355 = 0.01653 -0.00103 0.00040 -0.00075 AFIX 43 H4A 2 -0.100478 0.489891 0.857212 11.00000 -1.20000 AFIX 0 O5 5 0.387943 0.653062 0.854044 11.00000 0.01949 0.01898 = 0.02450 -0.00518 -0.00056 0.00157 AFIX 3 0.8400 H5A 2 0.342433 0.605952 0.836034 11.00000 -1.20000 H5B 2 0.437303 0.639272 0.913644 11.00000 -1.20000 AFIX 0 PART 1 O1 5 0.026454 0.413195 0.749838 11.00000 0.01896 0.02117 = 0.02721 -0.00705 0.00481 -0.00835 PART 0 N3 3 0.087456 0.649490 0.920373 11.00000 0.01647 0.01075 = 0.01548 -0.00153 0.00202 -0.00019 N5 3 -0.129993 0.603061 0.957620 11.00000 0.01633 0.01511 = 0.01988 -0.00050 0.00378 0.00020 N2 3 0.170237 0.529580 0.797072 11.00000 0.01664 0.01225 = 0.01890 -0.00476 0.00159 -0.00182 PART 2 O2 5 0.238883 0.414107 0.685509 11.00000 0.02141 0.01766 = 0.03601 -0.01059 0.01017 -0.00179 PART 0 N1 3 0.141659 0.451690 0.744486 11.00000 0.01818 0.01463 = 0.01846 -0.00168 0.00128 -0.00267 C1 1 0.065162 0.568913 0.863255 11.00000 0.01662 0.01146 = 0.01419 0.00094 -0.00229 0.00016 C3 1 -0.059911 0.750000 1.051166 10.50000 0.02014 0.01170 = 0.02181 0.00000 0.00527 0.00000 AFIX 23 H3A 2 -0.156066 0.750000 1.081140 10.50000 -1.20000 H3B 2 0.002602 0.750001 1.121788 10.50000 -1.20000 AFIX 0 C2 1 -0.035085 0.665959 0.976932 11.00000 0.01588 0.01273 = 0.01609 0.00184 0.00227 -0.00008 PART 1 O6 5 0.574321 0.588488 1.006619 21.00000 0.01913 0.05848 = 0.03714 0.00086 0.00252 0.00534 AFIX 3 0.8400 H6A 2 0.651911 0.576518 0.976839 21.00000 -1.20000 H6B 2 0.589121 0.616968 1.071229 21.00000 -1.20000 AFIX 0 PART 0 PART 2 O6A 5 0.589232 0.638229 1.017654 -21.00000 0.02055 0.06155 = 0.02831 0.01151 0.00137 0.00696 AFIX 3 0.8400 H6AA 2 0.589282 0.641899 1.093304 -21.00000 -1.20000 H6AB 2 0.656732 0.604379 1.001064 -21.00000 -1.20000 AFIX 0 HKLF 4 REM bwn18353-a in Pnma REM wR2 = 0.0940, GooF = S = 1.107, Restrained GooF = 1.103 for all data REM R1 = 0.0400 for 1739 Fo > 4sig(Fo) and 0.0427 for all 1846 data REM 134 parameters refined using 18 restraints END WGHT 0.0351 2.3571 REM Highest difference peak 0.613, deepest hole -0.588, 1-sigma level 0.079 Q1 1 0.6190 0.7500 1.1625 10.50000 0.05 0.61 Q2 1 0.0861 0.7500 0.7404 10.50000 0.05 0.38 Q3 1 0.0962 0.7298 0.6837 11.00000 0.05 0.33 Q4 1 0.1316 0.6930 0.9103 11.00000 0.05 0.28 Q5 1 -0.1141 0.6409 0.9406 11.00000 0.05 0.28 REM The information below was added by Olex2. REM REM R1 = 0.0400 for 1739 Fo > 4sig(Fo) and 0.0427 for all 6470 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.61, deepest hole -0.59 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0427 REM R1_gt = 0.0400 REM wR_ref = 0.0940 REM GOOF = 1.107 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 6470 REM Reflections_gt = 1739 REM Parameters = n/a REM Hole = -0.59 REM Peak = 0.61 REM Flack = n/a ; _cod_data_source_file c9ce01158g2.cif _cod_data_source_block bwn18353-a _cod_depositor_comments 'Adding full bibliography for 7233844--7233849.cif.' _cod_original_cell_volume 1566.3(5) _cod_database_code 7233848 _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 0.880 _shelx_estimated_absorpt_t_min 0.847 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All N(H) groups, All O(H) groups, All O(H,H) groups 2. Uiso/Uaniso restraints and constraints O6A \\sim O6: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01 Uanis(O6A) \\sim Ueq, Uanis(O6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 3. Others Sof(O6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(1) Sof(O6)=Sof(H6A)=Sof(H6B)=FVAR(1) 4.a Riding coordinates: O3(H3), O4(H4), O5(H5A,H5B), O6(H6A,H6B), O6A(H6AA,H6AB) 4.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B) 4.c Aromatic/amide H refined with riding coordinates: N4(H4A) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, 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 Ni1 Ni 0.23880(4) 0.750000 0.89423(4) 0.01345(14) Uani 1 2 d S T P . . O3 O 0.1849(3) 0.750000 0.7104(2) 0.0249(6) Uani 1 2 d S T P . . H3 H 0.205820 0.703960 0.668597 0.030 Uiso 1 1 d R . . . . O4 O 0.3000(3) 0.750000 1.0696(2) 0.0204(5) Uani 1 2 d S T P . . H4 H 0.295316 0.702510 1.112383 0.024 Uiso 1 1 d R . . . . N4 N -0.0637(2) 0.54082(14) 0.88517(17) 0.0154(4) Uani 1 1 d . . . . . H4A H -0.100478 0.489891 0.857212 0.018 Uiso 1 1 calc R . . . . O5 O 0.38794(17) 0.65306(12) 0.85404(16) 0.0210(4) Uani 1 1 d . . . . . H5A H 0.342433 0.605952 0.836034 0.025 Uiso 1 1 d R . . . . H5B H 0.437303 0.639272 0.913644 0.025 Uiso 1 1 d R . . . . O1 O 0.02645(18) 0.41319(12) 0.74984(16) 0.0224(4) Uani 1 1 d . . . A 1 N3 N 0.0875(2) 0.64949(13) 0.92037(17) 0.0142(4) Uani 1 1 d . . . . . N5 N -0.1300(2) 0.60306(14) 0.95762(18) 0.0171(4) Uani 1 1 d . . . . . N2 N 0.1702(2) 0.52958(13) 0.79707(18) 0.0159(4) Uani 1 1 d . . . . . O2 O 0.23888(18) 0.41411(12) 0.68551(18) 0.0250(4) Uani 1 1 d . . . B 2 N1 N 0.1417(2) 0.45169(13) 0.74449(18) 0.0171(4) Uani 1 1 d . . . . . C1 C 0.0652(2) 0.56891(15) 0.8633(2) 0.0141(5) Uani 1 1 d . . . . . C3 C -0.0599(4) 0.750000 1.0512(3) 0.0179(7) Uani 1 2 d S T P . . H3A H -0.156066 0.750000 1.081140 0.021 Uiso 1 2 calc RS T P . . H3B H 0.002602 0.750001 1.121788 0.021 Uiso 1 2 calc RS T P . . C2 C -0.0351(2) 0.66596(15) 0.9769(2) 0.0149(5) Uani 1 1 d . . . . . O6 O 0.5743(6) 0.5885(8) 1.0066(5) 0.0382(19) Uani 0.530(19) 1 d . U . C 1 H6A H 0.651911 0.576518 0.976839 0.046 Uiso 0.530(19) 1 d R . . C 1 H6B H 0.589121 0.616968 1.071229 0.046 Uiso 0.530(19) 1 d R . . C 1 O6A O 0.5892(7) 0.6382(9) 1.0177(6) 0.037(2) Uani 0.470(19) 1 d . U . C 2 H6AA H 0.589282 0.641899 1.093304 0.044 Uiso 0.470(19) 1 d R . . C 2 H6AB H 0.656732 0.604379 1.001064 0.044 Uiso 0.470(19) 1 d R . . C 2 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 Ni1 0.0148(2) 0.0119(2) 0.0137(2) 0.000 0.00073(15) 0.000 O3 0.0360(15) 0.0242(13) 0.0145(11) 0.000 -0.0022(11) 0.000 O4 0.0350(15) 0.0127(11) 0.0133(11) 0.000 -0.0044(10) 0.000 N4 0.0160(10) 0.0136(9) 0.0165(9) -0.0010(7) 0.0004(7) -0.0007(8) O5 0.0195(9) 0.0190(8) 0.0245(9) -0.0052(7) -0.0006(7) 0.0016(7) O1 0.0190(9) 0.0212(9) 0.0272(9) -0.0071(7) 0.0048(7) -0.0083(7) N3 0.0165(10) 0.0108(9) 0.0155(9) -0.0015(7) 0.0020(7) -0.0002(8) N5 0.0163(10) 0.0151(9) 0.0199(9) -0.0005(8) 0.0038(8) 0.0002(8) N2 0.0166(10) 0.0122(9) 0.0189(9) -0.0048(7) 0.0016(8) -0.0018(8) O2 0.0214(9) 0.0177(9) 0.0360(11) -0.0106(8) 0.0102(8) -0.0018(7) N1 0.0182(10) 0.0146(9) 0.0185(9) -0.0017(8) 0.0013(8) -0.0027(8) C1 0.0166(11) 0.0115(10) 0.0142(10) 0.0009(8) -0.0023(8) 0.0002(9) C3 0.0201(17) 0.0117(14) 0.0218(16) 0.000 0.0053(13) 0.000 C2 0.0159(11) 0.0127(10) 0.0161(10) 0.0018(8) 0.0023(9) -0.0001(9) O6 0.019(2) 0.058(5) 0.037(2) 0.001(3) 0.0025(18) 0.005(3) O6A 0.021(2) 0.062(6) 0.028(3) 0.012(3) 0.0014(19) 0.007(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' Ni Ni 0.3393 1.1124 '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 O4 Ni1 O3 177.40(11) . . O4 Ni1 O5 90.09(7) . . O4 Ni1 O5 90.09(8) . 7_575 O4 Ni1 N3 94.16(8) . 7_575 O4 Ni1 N3 94.16(8) . . O5 Ni1 O3 88.01(7) . . O5 Ni1 O3 88.02(8) 7_575 . O5 Ni1 O5 86.05(10) 7_575 . O5 Ni1 N3 175.49(7) 7_575 . O5 Ni1 N3 92.42(7) . . O5 Ni1 N3 92.42(7) 7_575 7_575 O5 Ni1 N3 175.49(7) . 7_575 N3 Ni1 O3 87.69(8) . . N3 Ni1 O3 87.69(8) 7_575 . N3 Ni1 N3 88.78(11) 7_575 . Ni1 O3 H3 118.3 . . Ni1 O3 H3 118.27(3) . 7_575 H3 O3 H3 106.0 . 7_575 Ni1 O4 H4 121.6 . . Ni1 O4 H4 121.58(2) . 7_575 H4 O4 H4 110.9 . 7_575 N5 N4 H4A 125.0 . . C1 N4 H4A 125.0 . . C1 N4 N5 110.01(19) . . Ni1 O5 H5A 104.0 . . Ni1 O5 H5B 113.1 . . H5A O5 H5B 106.9 . . C1 N3 Ni1 130.94(16) . . C1 N3 C2 103.21(19) . . C2 N3 Ni1 123.44(15) . . C2 N5 N4 103.15(19) . . N1 N2 C1 116.20(19) . . O1 N1 N2 123.9(2) . . O2 N1 N2 116.52(19) . . N4 C1 N3 109.3(2) . . N4 C1 N2 131.3(2) . . N3 C1 N2 119.4(2) . . H3A C3 H3B 108.2 . . C2 C3 H3A 109.7 7_575 . C2 C3 H3A 109.7 . . C2 C3 H3B 109.7 7_575 . C2 C3 H3B 109.7 . . C2 C3 C2 110.0(3) 7_575 . N3 C2 C3 122.5(2) . . N5 C2 N3 114.3(2) . . N5 C2 C3 123.2(2) . . H6A O6 H6B 106.5 . . H6AA O6A H6AB 104.8 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Ni1 O3 2.103(2) . Ni1 O4 2.032(2) . Ni1 O5 2.0703(17) 7_575 Ni1 O5 2.0704(17) . Ni1 N3 2.094(2) . Ni1 N3 2.0938(19) 7_575 O3 H3 0.8400 . O3 H3 0.8400 7_575 O4 H4 0.8401 . O4 H4 0.8402 7_575 N4 H4A 0.8800 . N4 N5 1.372(3) . N4 C1 1.337(3) . O5 H5A 0.8402 . O5 H5B 0.8401 . O1 N1 1.252(3) . N3 C1 1.351(3) . N3 C2 1.365(3) . N5 C2 1.317(3) . N2 N1 1.306(3) . N2 C1 1.380(3) . O2 N1 1.271(3) . C3 H3A 0.9900 . C3 H3B 0.9900 . C3 C2 1.495(3) 7_575 C3 C2 1.495(3) . O6 H6A 0.8400 . O6 H6B 0.8399 . O6A H6AA 0.8400 . O6A H6AB 0.8401 . 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 Ni1 N3 C1 N4 -161.95(15) . Ni1 N3 C1 N2 18.8(3) . Ni1 N3 C2 N5 163.15(15) . Ni1 N3 C2 C3 -15.0(3) . N4 N5 C2 N3 1.0(3) . N4 N5 C2 C3 179.2(2) . N5 N4 C1 N3 0.2(3) . N5 N4 C1 N2 179.3(2) . N1 N2 C1 N4 0.8(4) . N1 N2 C1 N3 179.9(2) . C1 N4 N5 C2 -0.7(2) . C1 N3 C2 N5 -0.9(3) . C1 N3 C2 C3 -179.1(2) . C1 N2 N1 O1 1.1(3) . C1 N2 N1 O2 -178.5(2) . C2 N3 C1 N4 0.4(2) . C2 N3 C1 N2 -178.9(2) . C2 C3 C2 N3 56.9(4) 7_575 C2 C3 C2 N5 -121.1(2) 7_575