#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:17:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180070 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/16/7051678.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_7051678
loop_
_publ_author_name
'Klapötke, Thomas M.'
'Sabaté, Carles Miró'
_publ_section_title
;
 New energetic compounds based on the nitrogen-rich
 5,5′-azotetrazolate anion ([C2N10]2−)
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1605
_journal_paper_doi               10.1039/b820381d
_journal_volume                  33
_journal_year                    2009
_chemical_formula_moiety         'C3 H8 N5, 0.5(C2 N10), 3(H2 O)'
_chemical_formula_sum            'C4 H14 N10 O3'
_chemical_formula_weight         250.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2008-06-26T15:07:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.481(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3101(3)
_cell_length_b                   6.5383(2)
_cell_length_c                   19.5637(5)
_cell_measurement_reflns_used    12627
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     1190.84(6)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford Xcalibur3 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4400
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.050
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0335P)²+0.3575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1500
_reflns_number_gt                1728
_reflns_number_total             2327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820381d.txt
_cod_data_source_block           13DMATZTx6H2O_ln471
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7051678
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.51187(18) 0.5100(2) 0.46859(8) 0.0329(4) Uani 1 1 d . . .
N9 N 0.39519(18) 0.5391(3) 0.36177(8) 0.0358(4) Uani 1 1 d . . .
N8 N 0.25906(18) 0.5517(3) 0.33961(9) 0.0379(4) Uani 1 1 d . . .
N7 N 0.17261(19) 0.5450(3) 0.39268(9) 0.0385(4) Uani 1 1 d . . .
N6 N 0.24944(18) 0.5280(3) 0.45069(9) 0.0358(4) Uani 1 1 d . . .
N2 N 0.15576(18) 0.0497(3) 0.36695(8) 0.0346(4) Uani 1 1 d . . .
N3 N 0.12342(19) 0.0390(3) 0.43349(9) 0.0370(4) Uani 1 1 d . . .
N4 N 0.24783(18) 0.0284(2) 0.46268(8) 0.0329(4) Uani 1 1 d . . .
N5 N 0.36158(18) 0.0311(3) 0.42130(8) 0.0339(4) Uani 1 1 d . . .
N1 N 0.3688(2) 0.0520(3) 0.30014(9) 0.0396(5) Uani 1 1 d . . .
C4 C 0.3854(2) 0.5252(3) 0.42921(10) 0.0303(4) Uani 1 1 d . . .
C1 C 0.3005(2) 0.0445(3) 0.35904(10) 0.0315(5) Uani 1 1 d . . .
C2 C 0.0437(2) 0.0612(4) 0.31466(12) 0.0508(6) Uani 1 1 d . . .
H2A H -0.0506 0.0625 0.3365 0.076 Uiso 1 1 calc R . .
H2B H 0.0506 -0.0577 0.2844 0.076 Uiso 1 1 calc R . .
H2C H 0.0558 0.1867 0.2879 0.076 Uiso 1 1 calc R . .
C3 C 0.2642(3) 0.0167(4) 0.53680(10) 0.0417(5) Uani 1 1 d . . .
H3A H 0.3666 0.0100 0.5488 0.063 Uiso 1 1 calc R . .
H3B H 0.2156 -0.1060 0.5537 0.063 Uiso 1 1 calc R . .
H3C H 0.2216 0.1383 0.5577 0.063 Uiso 1 1 calc R . .
O1 O 0.83292(18) 0.5033(4) 0.19510(9) 0.0529(5) Uani 1 1 d . . .
O2 O 0.6855(2) 0.5829(3) 0.31510(9) 0.0525(5) Uani 1 1 d . . .
O3 O 0.1294(2) 0.5385(3) 0.58690(10) 0.0622(6) Uani 1 1 d . . .
H1A H 0.314(3) 0.048(4) 0.2583(15) 0.058(7) Uiso 1 1 d . . .
H1B H 0.466(3) 0.047(4) 0.3007(14) 0.056(8) Uiso 1 1 d . . .
H32 H 0.147(4) 0.514(5) 0.538(2) 0.086(10) Uiso 1 1 d . . .
H21 H 0.601(4) 0.555(5) 0.3261(17) 0.078(10) Uiso 1 1 d . . .
H31 H 0.042(4) 0.493(4) 0.5918(17) 0.080(11) Uiso 1 1 d . . .
H22 H 0.748(4) 0.539(5) 0.3500(19) 0.085(11) Uiso 1 1 d . . .
H12 H 0.787(4) 0.528(5) 0.2366(19) 0.089(11) Uiso 1 1 d . . .
H11 H 0.823(3) 0.373(5) 0.1907(15) 0.074(11) Uiso 1 1 d . . .
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
N10 N10 C4 112.9(2) 3_666 . ?
C4 N9 N8 104.68(16) . . ?
N7 N8 N9 108.97(16) . . ?
N8 N7 N6 110.12(16) . . ?
C4 N6 N7 103.57(16) . . ?
N3 N2 C1 109.91(17) . . ?
N3 N2 C2 121.29(17) . . ?
C1 N2 C2 128.80(17) . . ?
N4 N3 N2 102.99(16) . . ?
N3 N4 N5 116.36(16) . . ?
N3 N4 C3 121.96(17) . . ?
N5 N4 C3 121.68(17) . . ?
N4 N5 C1 102.60(16) . . ?
C1 N1 H1A 119.3(17) . . ?
C1 N1 H1B 118.5(17) . . ?
H1A N1 H1B 122(2) . . ?
N9 C4 N6 112.65(18) . . ?
N9 C4 N10 119.05(17) . . ?
N6 C4 N10 128.30(18) . . ?
N1 C1 N5 126.16(19) . . ?
N1 C1 N2 125.70(19) . . ?
N5 C1 N2 108.15(17) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
H12 O1 H11 102(3) . . ?
H21 O2 H22 109(3) . . ?
H32 O3 H31 103(3) . . ?
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
N10 N10 1.257(3) 3_666 ?
N10 C4 1.406(3) . ?
N9 C4 1.326(2) . ?
N9 N8 1.339(2) . ?
N8 N7 1.320(2) . ?
N7 N6 1.341(3) . ?
N6 C4 1.337(3) . ?
N2 N3 1.340(2) . ?
N2 C1 1.358(3) . ?
N2 C2 1.457(3) . ?
N3 N4 1.289(2) . ?
N4 N5 1.339(2) . ?
N4 C3 1.459(2) . ?
N5 C1 1.343(3) . ?
N1 C1 1.322(3) . ?
N1 H1A 0.96(3) . ?
N1 H1B 0.91(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
O1 H12 0.94(4) . ?
O1 H11 0.86(4) . ?
O2 H21 0.84(4) . ?
O2 H22 0.94(4) . ?
O3 H32 0.98(4) . ?
O3 H31 0.88(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
N1 H1A N8 0.96(3) 2.03(3) 2.973(3) 168(2) 2_545
N1 H1B O1 0.91(3) 1.89(3) 2.796(3) 173(2) 2_645
O3 H32 N6 0.98(4) 1.97(4) 2.899(3) 158(3) .
O2 H21 N9 0.84(4) 2.04(4) 2.875(2) 169(3) .
O3 H31 N7 0.88(4) 2.03(4) 2.895(3) 167(3) 3_566
O2 H22 O3 0.94(4) 1.75(4) 2.687(3) 177(3) 3_666
O1 H12 O2 0.94(4) 1.84(4) 2.778(2) 176(3) .
O1 H11 O2 0.86(4) 1.90(4) 2.761(3) 175(3) 2_645
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
C4 N9 N8 N7 -0.1(2) . . . . ?
N9 N8 N7 N6 0.0(2) . . . . ?
N8 N7 N6 C4 0.1(2) . . . . ?
C1 N2 N3 N4 0.1(2) . . . . ?
C2 N2 N3 N4 179.18(19) . . . . ?
N2 N3 N4 N5 0.0(2) . . . . ?
N2 N3 N4 C3 179.25(17) . . . . ?
N3 N4 N5 C1 -0.1(2) . . . . ?
C3 N4 N5 C1 -179.38(17) . . . . ?
N8 N9 C4 N6 0.1(2) . . . . ?
N8 N9 C4 N10 -179.84(16) . . . . ?
N7 N6 C4 N9 -0.1(2) . . . . ?
N7 N6 C4 N10 179.84(18) . . . . ?
N10 N10 C4 N9 -177.4(2) 3_666 . . . ?
N10 N10 C4 N6 2.6(3) 3_666 . . . ?
N4 N5 C1 N1 -179.96(19) . . . . ?
N4 N5 C1 N2 0.2(2) . . . . ?
N3 N2 C1 N1 179.95(19) . . . . ?
C2 N2 C1 N1 1.0(3) . . . . ?
N3 N2 C1 N5 -0.2(2) . . . . ?
C2 N2 C1 N5 -179.2(2) . . . . ?
