#------------------------------------------------------------------------------
#$Date: 2016-03-21 00:21:50 +0100 (lun 21 de mar de 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/11/4001176.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_4001176
loop_
_publ_author_name
'Klapötke, Thomas M.'
'Stierstorfer, Jörg'
'Wallek, Andreas U.'
_publ_section_title
;
 Nitrogen-Rich Salts of 1-Methyl-5-nitriminotetrazolate: An Auspicious
 Class of Thermally Stable Energetic Materials
;
_journal_issue                   13
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4519
_journal_paper_doi               10.1021/cm8004166
_journal_volume                  20
_journal_year                    2008
_chemical_formula_moiety         'C2 H3 N6 O2, C H6 N3'
_chemical_formula_sum            'C3 H9 N9 O2'
_chemical_formula_weight         203.19
_chemical_name_common            'guanidinium 1-methyl-5-nitriminotetrazolate'
_chemical_name_systematic        'guanidinium 1-methyl-5-nitriminotetrazolate'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             25-Sep-07
_audit_creation_method           SHELXL-97
_audit_update_record             25-Sep-07
_cell_angle_alpha                90.00
_cell_angle_beta                 102.457(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.2356(8)
_cell_length_b                   6.8969(2)
_cell_length_c                   12.1761(4)
_cell_measurement_reflns_used    6330
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      3.134
_cell_volume                     1741.33(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
'PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_orient_matrix_UB_11      0.0043694
_diffrn_orient_matrix_UB_12      0.1135632
_diffrn_orient_matrix_UB_13      0.0521600
_diffrn_orient_matrix_UB_21      -0.0086773
_diffrn_orient_matrix_UB_22      0.0899448
_diffrn_orient_matrix_UB_23      -0.0659623
_diffrn_orient_matrix_UB_31      -0.0472373
_diffrn_orient_matrix_UB_32      -0.0060178
_diffrn_orient_matrix_UB_33      -0.0015806
_diffrn_radiation_collimation    0.25
_diffrn_radiation_monochromator  'vertically mounted graphite crystal'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5055
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         3.45
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0119(15)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                1330
_reflns_number_total             1574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm8004166-file007.cif
_cod_data_source_block           ln514
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4001176
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.19385(9) 0.4725(3) -0.08355(14) 0.0414(6) Uani 1 1 d
O2 O 0.27256(8) 0.4770(3) 0.06437(15) 0.0401(6) Uani 1 1 d
N1 N 0.07713(10) 0.2908(3) 0.11084(18) 0.0303(5) Uani 1 1 d
N2 N 0.01813(11) 0.2491(4) 0.0496(2) 0.0397(6) Uani 1 1 d
N3 N 0.02129(11) 0.2728(4) -0.0544(2) 0.0438(7) Uani 1 1 d
N4 N 0.08101(10) 0.3290(4) -0.06455(18) 0.0370(6) Uani 1 1 d
N5 N 0.17873(9) 0.3816(3) 0.08756(17) 0.0289(5) Uani 1 1 d
N6 N 0.21414(10) 0.4444(3) 0.01934(17) 0.0297(5) Uani 1 1 d
N7 N 0.10695(12) 0.7721(4) 0.2083(2) 0.0339(6) Uani 1 1 d
N8 N 0.12963(12) 0.8530(4) 0.03777(18) 0.0325(6) Uani 1 1 d
N9 N 0.20917(11) 0.8683(4) 0.1971(2) 0.0384(6) Uani 1 1 d
C1 C 0.11572(12) 0.3400(4) 0.0401(2) 0.0266(6) Uani 1 1 d
C2 C 0.09249(16) 0.2756(5) 0.2329(2) 0.0385(7) Uani 1 1 d
C3 C 0.14883(12) 0.8305(4) 0.1484(2) 0.0273(6) Uani 1 1 d
H8B H 0.1583(14) 0.903(4) 0.005(2) 0.027(7) Uiso 1 1 d
H8A H 0.0916(15) 0.831(4) 0.008(2) 0.026(7) Uiso 1 1 d
H7A H 0.1235(14) 0.744(4) 0.274(3) 0.032(8) Uiso 1 1 d
H21 H 0.1385(17) 0.264(5) 0.262(3) 0.046(9) Uiso 1 1 d
H22 H 0.0760(19) 0.386(6) 0.261(3) 0.073(12) Uiso 1 1 d
H7B H 0.0676(18) 0.761(5) 0.175(3) 0.050(10) Uiso 1 1 d
H9A H 0.2370(16) 0.914(5) 0.157(3) 0.048(9) Uiso 1 1 d
H9B H 0.2191(16) 0.879(5) 0.273(3) 0.055(10) Uiso 1 1 d
H23 H 0.0721(19) 0.162(6) 0.256(3) 0.072(12) Uiso 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
O1 0.0341(11) 0.0676(15) 0.0223(9) 0.0117(9) 0.0057(8) -0.0012(10)
O2 0.0241(10) 0.0628(14) 0.0330(10) 0.0053(9) 0.0053(8) -0.0088(9)
N1 0.0268(11) 0.0360(13) 0.0294(11) -0.0041(10) 0.0092(9) -0.0057(9)
N2 0.0276(12) 0.0503(15) 0.0420(14) -0.0064(11) 0.0091(10) -0.0084(11)
N3 0.0307(13) 0.0614(17) 0.0374(14) -0.0015(12) 0.0030(10) -0.0106(12)
N4 0.0281(12) 0.0527(15) 0.0288(12) 0.0010(11) 0.0034(9) -0.0063(11)
N5 0.0246(11) 0.0405(13) 0.0227(10) 0.0014(9) 0.0075(9) -0.0051(9)
N6 0.0262(11) 0.0378(13) 0.0255(11) 0.0026(9) 0.0063(9) -0.0010(10)
N7 0.0301(13) 0.0479(15) 0.0236(12) 0.0042(11) 0.0055(10) -0.0060(11)
N8 0.0263(12) 0.0471(15) 0.0238(11) 0.0034(10) 0.0051(10) -0.0096(11)
N9 0.0280(12) 0.0600(17) 0.0259(12) -0.0005(12) 0.0027(10) -0.0105(11)
C1 0.0272(13) 0.0282(13) 0.0253(12) -0.0015(10) 0.0078(10) -0.0013(10)
C2 0.0440(18) 0.0478(19) 0.0269(14) -0.0053(13) 0.0146(13) -0.0116(15)
C3 0.0277(13) 0.0292(13) 0.0252(12) -0.0016(11) 0.0059(10) -0.0003(10)
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.020000
0 0 -1 0.030000
-8 12 1 0.120000
8 0 -1 0.120000
-11 -1 1 0.089000
-8 -11 1 0.105000
-8 -4 1 0.072000
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C1 108.7(2)
N2 N1 C2 121.9(2)
C1 N1 C2 129.4(2)
N3 N2 N1 106.1(2)
N2 N3 N4 111.9(2)
C1 N4 N3 105.4(2)
N6 N5 C1 116.4(2)
O1 N6 O2 120.1(2)
O1 N6 N5 124.5(2)
O2 N6 N5 115.4(2)
C3 N7 H7A 114(2)
C3 N7 H7B 118(2)
H7A N7 H7B 128(3)
C3 N8 H8B 114.6(18)
C3 N8 H8A 118.4(19)
H8B N8 H8A 127(3)
C3 N9 H9A 121(2)
C3 N9 H9B 118(2)
H9A N9 H9B 119(3)
N4 C1 N1 108.0(2)
N4 C1 N5 134.9(2)
N1 C1 N5 117.1(2)
N1 C2 H21 111.2(18)
N1 C2 H22 107(2)
H21 C2 H22 111(3)
N1 C2 H23 110(2)
H21 C2 H23 108(3)
H22 C2 H23 109(3)
N9 C3 N7 120.9(2)
N9 C3 N8 119.3(2)
N7 C3 N8 119.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N6 1.249(3)
O2 N6 1.264(3)
N1 N2 1.344(3)
N1 C1 1.354(3)
N1 C2 1.455(3)
N2 N3 1.292(3)
N3 N4 1.357(3)
N4 C1 1.330(3)
N5 N6 1.309(3)
N5 C1 1.368(3)
N7 C3 1.329(3)
N7 H7A 0.82(3)
N7 H7B 0.85(4)
N8 C3 1.329(3)
N8 H8B 0.86(3)
N8 H8A 0.82(3)
N9 C3 1.317(3)
N9 H9A 0.90(4)
N9 H9B 0.90(4)
C2 H21 0.97(3)
C2 H22 0.94(4)
C2 H23 0.97(4)
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
N8 H8B O2 0.86(3) 2.03(3) 2.890(3) 178(3) 7_565
N8 H8A N2 0.82(3) 2.35(3) 3.167(3) 172(3) 5_565
N8 H8A N3 0.82(3) 2.67(3) 3.368(3) 143(2) 5_565
N7 H7A N4 0.82(3) 2.39(3) 3.016(3) 134(2) 6_566
N7 H7A O1 0.82(3) 2.52(3) 3.265(3) 151(3) 6_566
N7 H7B N3 0.85(4) 2.14(4) 2.970(3) 166(3) 5_565
N9 H9A O1 0.90(4) 2.04(4) 2.930(3) 174(3) 7_565
N9 H9B O2 0.90(4) 2.07(4) 2.942(3) 164(3) 4
N9 H9B N5 0.90(4) 2.45(4) 3.139(3) 133(3) 4
N9 H9B N6 0.90(4) 2.66(4) 3.524(3) 161(3) 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
C1 N1 N2 N3 -0.1(3)
C2 N1 N2 N3 -178.5(3)
N1 N2 N3 N4 0.2(3)
N2 N3 N4 C1 -0.2(3)
C1 N5 N6 O1 1.8(4)
C1 N5 N6 O2 -178.2(2)
N3 N4 C1 N1 0.1(3)
N3 N4 C1 N5 177.5(3)
N2 N1 C1 N4 0.0(3)
C2 N1 C1 N4 178.2(3)
N2 N1 C1 N5 -177.9(2)
C2 N1 C1 N5 0.3(4)
N6 N5 C1 N4 8.3(4)
N6 N5 C1 N1 -174.5(2)
