data_fx372 _publ_contact_author_name 'Thomas M. Klapo\"tke' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_author_name ; Fischer, Niko Klap\"otke, Thomas M. Lux, K. Martin, Franz. A. Stierstorfer, Joerg ; _publ_author_address ; Fischer, N. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Lux, K. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Martin, F. A. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Klapoetke, T. M. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland Stierstorfer, J. Department Chemie Ludwig-Maximilians Universit\"at Butenandtstrasse 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'tmk@cup.uni-muenchen.de' _publ_contact_author_fax '+49-89-2180-77491' _publ_contact_author_phone '+49-89-2180-77492' _publ_requested_journal 'Crystals' _publ_section_title ; Inorganic Amino-Nitro-Guanidinium (ANQ) Derivatives ; _publ_section_abstract ? _publ_section_comment ? _audit_author_name 'Joerg Stierstorfer' _audit_block_code ? _audit_creation_method ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _audit_creation_date ; 'Fri Apr 13 14:30:20 2012' ; _audit_update_record ? _chemical_name_systematic 'aminonitroguanidinium bromide monohydrate' _chemical_compound_source ? _chemical_name_common 'aminonitroguanidinium bromide monohydrate' _chemical_formula_moiety 'C H6 N5 O2, Br, H2 O ' _chemical_formula_sum 'C H8 Br N5 O3' _chemical_formula_weight 218.03 _cell_length_a 8.0261(5) _cell_length_b 12.7412(7) _cell_length_c 7.9296(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.051(9) _cell_angle_gamma 90.00 _cell_volume 715.64(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1218 _cell_measurement_theta_min 4.3174 _cell_measurement_theta_max 33.5895 _cell_special_details ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 5.708 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.1625 _exptl_absorpt_correction_T_max 0.8038 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 173 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 3576 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.33 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 1395 _reflns_number_gt 1182 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0723651000 _diffrn_orient_matrix_UB_12 0.0358905000 _diffrn_orient_matrix_UB_13 -0.0121617000 _diffrn_orient_matrix_UB_21 0.0600658000 _diffrn_orient_matrix_UB_22 0.0424957000 _diffrn_orient_matrix_UB_23 0.0071723000 _diffrn_orient_matrix_UB_31 -0.0344767000 _diffrn_orient_matrix_UB_32 -0.0013090000 _diffrn_orient_matrix_UB_33 -0.1003768000 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number ? _symmetry_space_group_name_Hall '-P 2ybc' 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' 'Br' 'Br' -0.2901 2.4595 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.681 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.117 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_hydrogen_treatment mixed _atom_sites_solution_hydrogens geom _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1395 _refine_ls_number_parameters 123 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0636 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4448(4) 0.1577(2) 0.4894(3) 0.0240(6) Uani 1 1 d . . . O2 O 0.6160(4) 0.1859(2) 0.7915(4) 0.0256(6) Uani 1 1 d . . . N1 N 0.4278(4) 0.0506(2) 0.7145(4) 0.0143(6) Uani 1 1 d . . . N2 N 0.4959(4) 0.1346(2) 0.6588(4) 0.0161(7) Uani 1 1 d . . . N3 N 0.2292(4) -0.0886(2) 0.6449(4) 0.0150(7) Uani 1 1 d D . . N4 N 0.3299(5) -0.1082(3) 0.8464(5) 0.0152(7) Uani 1 1 d . . . N5 N 0.2095(4) 0.0025(3) 0.3900(4) 0.0202(7) Uani 1 1 d D . . C1 C 0.2936(5) -0.0073(3) 0.5774(5) 0.0132(7) Uani 1 1 d . . . Br1 Br 0.19081(5) 0.39060(3) 0.48465(5) 0.01900(14) Uani 1 1 d . . . O3 O 0.9332(4) 0.2556(2) 0.6275(4) 0.0193(6) Uani 1 1 d . . . H4A H 0.450(6) -0.129(3) 0.879(5) 0.012(10) Uiso 1 1 d . . . H4C H 0.279(6) -0.165(4) 0.873(6) 0.036(13) Uiso 1 1 d . . . H3A H 1.006(6) 0.238(3) 0.729(6) 0.026(13) Uiso 1 1 d . . . H5A H 0.243(5) 0.055(2) 0.337(5) 0.018(10) Uiso 1 1 d D . . H4B H 0.320(6) -0.047(3) 0.903(6) 0.027(11) Uiso 1 1 d . . . H3B H 0.986(6) 0.287(3) 0.582(6) 0.030(14) Uiso 1 1 d . . . H5B H 0.117(4) -0.043(2) 0.319(5) 0.029(12) Uiso 1 1 d D . . H3 H 0.198(6) -0.1477(19) 0.577(5) 0.037(13) Uiso 1 1 d 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 O1 0.0324(15) 0.0239(15) 0.0144(13) 0.0056(12) 0.0099(12) -0.0032(13) O2 0.0304(15) 0.0228(16) 0.0174(14) -0.0056(13) 0.0062(13) -0.0148(13) N1 0.0168(15) 0.0133(16) 0.0134(15) 0.0000(13) 0.0075(13) -0.0033(13) N2 0.0188(16) 0.0132(16) 0.0178(16) -0.0004(14) 0.0099(14) -0.0001(14) N3 0.0180(16) 0.0121(17) 0.0121(15) -0.0005(14) 0.0048(14) -0.0024(14) N4 0.0213(18) 0.0107(17) 0.0146(16) 0.0008(14) 0.0094(15) -0.0024(15) N5 0.0207(17) 0.0235(19) 0.0110(16) -0.0006(15) 0.0028(14) -0.0061(15) C1 0.0142(17) 0.0105(18) 0.0168(18) 0.0010(16) 0.0089(15) 0.0046(15) Br1 0.0173(2) 0.0224(2) 0.0158(2) -0.00136(16) 0.00648(17) -0.00392(16) O3 0.0182(14) 0.0208(16) 0.0158(15) 0.0033(13) 0.0055(13) 0.0000(13) 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 O1 N2 1.241(4) . ? O2 N2 1.229(4) . ? N1 C1 1.337(4) . ? N1 N2 1.366(4) . ? N3 C1 1.374(4) . ? N3 N4 1.433(4) . ? N3 H3 0.890(10) . ? N4 H4A 0.91(4) . ? N4 H4C 0.90(4) . ? N4 H4B 0.92(4) . ? N5 C1 1.318(4) . ? N5 H5A 0.895(10) . ? N5 H5B 0.896(10) . ? O3 H3A 0.78(4) . ? O3 H3B 0.78(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 C1 N1 N2 117.5(3) . . ? O2 N2 O1 121.8(3) . . ? O2 N2 N1 114.3(3) . . ? O1 N2 N1 123.8(3) . . ? C1 N3 N4 116.6(3) . . ? C1 N3 H3 117(3) . . ? N4 N3 H3 112(3) . . ? N3 N4 H4A 109(2) . . ? N3 N4 H4C 109(3) . . ? H4A N4 H4C 103(3) . . ? N3 N4 H4B 105(2) . . ? H4A N4 H4B 116(3) . . ? H4C N4 H4B 114(4) . . ? C1 N5 H5A 119(2) . . ? C1 N5 H5B 119(3) . . ? H5A N5 H5B 122(4) . . ? N5 C1 N1 130.9(3) . . ? N5 C1 N3 115.1(3) . . ? N1 C1 N3 114.0(3) . . ? H3A O3 H3B 109(4) . . ? 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 C1 N1 N2 O2 178.5(3) . . . . ? C1 N1 N2 O1 -2.5(5) . . . . ? N2 N1 C1 N5 -0.8(5) . . . . ? N2 N1 C1 N3 -178.4(3) . . . . ? N4 N3 C1 N5 174.0(3) . . . . ? N4 N3 C1 N1 -8.0(4) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 N4 H4A Br1 0.91(4) 2.57(4) 3.427(3) 156(3) 2_646 N4 H4C O3 0.90(4) 1.98(4) 2.815(4) 153(4) 2_646 N4 H4C O2 0.90(4) 2.40(4) 2.871(4) 113(3) 3_657 O3 H3A Br1 0.78(4) 2.48(5) 3.203(3) 156(4) 4_666 N5 H5A O1 0.895(10) 1.99(3) 2.588(4) 123(3) . N5 H5A Br1 0.895(10) 2.71(3) 3.428(3) 138(3) 4_565 N4 H4B Br1 0.92(4) 2.47(4) 3.360(3) 163(3) 4_566 O3 H3B Br1 0.78(4) 2.50(4) 3.275(3) 172(4) 1_655 N5 H5B Br1 0.896(10) 2.654(19) 3.493(3) 156(3) 2_545 N3 H3 O3 0.890(10) 2.005(16) 2.871(4) 164(4) 3_656 N3 H3 O2 0.890(10) 2.52(4) 3.075(4) 121(3) 2_646 _geom_special_details ? _iucr_refine_instructions_details ; TITL lsg in P2(1)/c CELL 0.71073 8.0261 12.7412 7.9296 90.000 118.051 90.000 ZERR 4.00 0.0005 0.0007 0.0005 0.000 0.009 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C BR N O H UNIT 4 4 20 12 32 MERG 2 OMIT -2.00 52.00 DFIX 0.90 0.01 N5 H5A N5 H5B DFIX 0.90 0.01 N3 H3 EQIV $1 -x+1, y-1/2, -z+3/2 EQIV $2 -x+1, -y, -z+2 EQIV $3 x+1, -y+1/2, z+1/2 EQIV $4 x, -y+1/2, z-1/2 EQIV $5 x, -y+1/2, z+1/2 EQIV $6 x+1, y, z EQIV $7 -x, y-1/2, -z+1/2 EQIV $8 -x+1, -y, -z+1 HTAB N4 Br1_$1 HTAB N4 O3_$1 HTAB N4 O2_$2 HTAB O3 Br1_$3 HTAB N5 O1 HTAB N5 Br1_$4 HTAB N4 Br1_$5 HTAB O3 Br1_$6 HTAB N5 Br1_$7 HTAB N3 O3_$8 HTAB N3 O2_$1 FMAP 2 PLAN 20 SIZE 0.04 0.21 0.50 ACTA BOND $H CONF L.S. 5 TEMP -100.00 WGHT 0.022500 FVAR 0.64076 O1 4 0.444842 0.157653 0.489443 11.00000 0.03238 0.02394 = 0.01437 0.00561 0.00990 -0.00323 O2 4 0.615963 0.185949 0.791476 11.00000 0.03040 0.02281 = 0.01740 -0.00560 0.00619 -0.01479 N1 3 0.427821 0.050592 0.714535 11.00000 0.01677 0.01333 = 0.01341 0.00003 0.00749 -0.00330 N2 3 0.495872 0.134598 0.658770 11.00000 0.01877 0.01317 = 0.01784 -0.00039 0.00991 -0.00014 N3 3 0.229221 -0.088634 0.644919 11.00000 0.01802 0.01212 = 0.01212 -0.00050 0.00482 -0.00235 N4 3 0.329871 -0.108232 0.846367 11.00000 0.02132 0.01074 = 0.01460 0.00077 0.00938 -0.00241 N5 3 0.209463 0.002524 0.389953 11.00000 0.02065 0.02350 = 0.01096 -0.00057 0.00281 -0.00610 C1 1 0.293573 -0.007332 0.577388 11.00000 0.01423 0.01055 = 0.01685 0.00097 0.00891 0.00458 BR1 2 0.190809 0.390596 0.484652 11.00000 0.01727 0.02237 = 0.01579 -0.00136 0.00648 -0.00392 O3 4 0.933159 0.255559 0.627491 11.00000 0.01824 0.02081 = 0.01581 0.00327 0.00548 0.00001 H4A 5 0.449871 -0.129477 0.878863 11.00000 0.01236 H4C 5 0.279330 -0.164838 0.873088 11.00000 0.03608 H3A 5 1.006041 0.237544 0.729173 11.00000 0.02624 H5A 5 0.242653 0.055161 0.337106 11.00000 0.01842 H4B 5 0.319824 -0.047227 0.903183 11.00000 0.02658 H3B 5 0.985757 0.286711 0.582105 11.00000 0.03002 H5B 5 0.117321 -0.042694 0.319377 11.00000 0.02862 H3 5 0.197675 -0.147749 0.577082 11.00000 0.03716 HKLF 4 REM lsg in P2(1)/c REM R1 = 0.0325 for 1182 Fo > 4sig(Fo) and 0.0411 for all 1395 data REM 123 parameters refined using 3 restraints END WGHT 0.0225 0.0000 REM Highest difference peak 0.681, deepest hole -0.772, 1-sigma level 0.117 Q1 1 0.2389 0.3908 0.3804 11.00000 0.05 0.68 Q2 1 0.1460 0.3913 0.6145 11.00000 0.05 0.59 Q3 1 0.2626 0.0235 0.9265 11.00000 0.05 0.48 Q4 1 1.1263 0.3069 0.5567 11.00000 0.05 0.42 Q5 1 0.4867 0.0013 0.8158 11.00000 0.05 0.39 Q6 1 0.1200 0.4696 0.5586 11.00000 0.05 0.39 Q7 1 1.2723 0.2299 0.8419 11.00000 0.05 0.38 Q8 1 0.2450 0.2978 0.4202 11.00000 0.05 0.38 Q9 1 0.1230 -0.0442 0.6499 11.00000 0.05 0.37 Q10 1 0.8434 0.2059 0.8076 11.00000 0.05 0.37 Q11 1 0.3369 0.0591 0.7403 11.00000 0.05 0.36 Q12 1 0.6153 0.2681 0.7206 11.00000 0.05 0.35 Q13 1 0.9638 0.4012 0.5025 11.00000 0.05 0.33 Q14 1 0.3727 0.3639 0.6383 11.00000 0.05 0.33 Q15 1 0.3191 -0.0164 0.3080 11.00000 0.05 0.32 Q16 1 0.4810 0.0825 0.3759 11.00000 0.05 0.32 Q17 1 0.9839 0.2112 0.8193 11.00000 0.05 0.32 Q18 1 0.0538 0.3861 0.4854 11.00000 0.05 0.32 Q19 1 0.2651 0.4412 0.6628 11.00000 0.05 0.32 Q20 1 0.0319 0.3866 0.3216 11.00000 0.05 0.32 ;