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#$Date: 2016-03-21 02:28:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178392 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/14/4021467.cif $
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#
# 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_4021467
loop_
_publ_author_name
'Konstantin Karaghiosoff'
'Thomas M. Klapötke'
'Peter Mayer'
'Holger Piotrowski'
'Kurt Polborn'
'Rodney L. Willer'
'Jan J. Weigand'
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universität
Butenandtstrasse 5-13 (Haus D)
D-81377 München
Bundesrepublik Deutschland
;
_publ_contact_author_email       tmk@cup.uni-muenchen.de
_publ_contact_author_fax         +49-89-2180-77492
_publ_contact_author_name        'Thomas M. Klapötke '
_publ_contact_author_phone       +49-89-2180-77491
_publ_section_title
;
 N-Nitroso- and N-Nitraminotetrazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1295
_journal_page_last               1305
_journal_paper_doi               10.1021/jo0513820
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C3 H6 N6 O2'
_chemical_formula_sum            'C3 H6 N6 O2'
_chemical_formula_weight         158.119
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Mayer, P.'
_audit_block_code                N6O2C3H6_g096_klapoetke
_audit_creation_date             29-Jun-02
_audit_creation_method           'form98_1/compatible with shelxl97-2'
_audit_update_record             12-Apr-05
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.9553(4)
_cell_length_b                   13.2837(10)
_cell_length_c                   17.4438(15)
_cell_measurement_reflns_used    2889
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     1379.95(18)
_computing_cell_refinement       'Stoe IPDS software (Darmstadt, Germany)'
_computing_data_collection       'Stoe IPDS software (Darmstadt, Germany)'
_computing_data_reduction        'Stoe IPDS software (Darmstadt, Germany)'
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of Göttingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'image-plate area detector'
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'area detection'
_diffrn_orient_matrix_type
;first index: i in a~i~^*^, second: diffractometer xyz
 e.g. UB_21,UB_22,UB_23 are the xyz components of b^*^
;
_diffrn_orient_matrix_UB_11      0.063971
_diffrn_orient_matrix_UB_12      0.154195
_diffrn_orient_matrix_UB_13      -0.018120
_diffrn_orient_matrix_UB_21      -0.064761
_diffrn_orient_matrix_UB_22      0.029721
_diffrn_orient_matrix_UB_23      0.024284
_diffrn_orient_matrix_UB_31      0.019424
_diffrn_orient_matrix_UB_32      -0.001724
_diffrn_orient_matrix_UB_33      0.053909
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6175
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.34
_diffrn_source_current           50_mA
_diffrn_source_power             2.75_kW
_diffrn_source_type              'Spellman DF4 Series'
_diffrn_source_voltage           55_kV
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'Absorption correction with XRed, rev 1.09, STOE (Darmstadt, Germany)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.52218(20)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0411
_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)+(0.0534P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                759
_reflns_number_total             1199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0513820rom20050704_032924.cif
_cod_database_code               4021467
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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 0.6947(4) 0.07165(15) 0.00455(10) 0.0560(6) Uani 1 1 d
O2 O 0.4477(3) 0.19260(16) -0.00489(9) 0.0503(5) Uani 1 1 d
N1 N 0.3194(3) 0.27088(14) 0.14882(9) 0.0240(4) Uani 1 1 d
N2 N 0.1206(4) 0.29204(16) 0.18115(10) 0.0322(5) Uani 1 1 d
N3 N 0.0134(4) 0.20736(16) 0.18788(10) 0.0351(5) Uani 1 1 d
N4 N 0.1381(3) 0.13002(15) 0.15975(9) 0.0307(5) Uani 1 1 d
N5 N 0.5124(3) 0.12098(15) 0.10858(9) 0.0291(5) Uani 1 1 d
N6 N 0.5526(4) 0.12862(19) 0.03029(11) 0.0396(6) Uani 1 1 d
C1 C 0.3246(4) 0.17176(16) 0.13604(10) 0.0229(5) Uani 1 1 d
C2 C 0.4899(5) 0.34748(19) 0.13516(15) 0.0341(6) Uani 1 1 d
H2A H 0.446(7) 0.407(3) 0.1658(18) 0.086(12) Uiso 1 1 d
H2B H 0.506(5) 0.360(2) 0.0844(19) 0.065(9) Uiso 1 1 d
H2C H 0.619(7) 0.330(3) 0.1600(18) 0.076(11) Uiso 1 1 d
C3 C 0.5998(5) 0.0330(2) 0.14883(17) 0.0392(7) Uani 1 1 d
H3A H 0.758(7) 0.028(3) 0.1457(17) 0.073(10) Uiso 1 1 d
H3B H 0.535(6) -0.026(3) 0.1292(15) 0.060(9) Uiso 1 1 d
H3C H 0.559(5) 0.039(2) 0.2000(16) 0.048(8) 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 0.0449(13) 0.0552(13) 0.0678(12) -0.0246(10) 0.0316(10) -0.0070(11)
O2 0.0572(13) 0.0623(13) 0.0314(9) 0.0031(8) 0.0085(8) 0.0010(11)
N1 0.0238(11) 0.0244(10) 0.0237(9) 0.0014(7) -0.0002(7) 0.0009(9)
N2 0.0301(12) 0.0355(12) 0.0310(9) 0.0003(8) 0.0028(8) 0.0093(10)
N3 0.0283(12) 0.0405(13) 0.0366(10) 0.0008(8) 0.0078(9) 0.0025(11)
N4 0.0265(12) 0.0306(11) 0.0349(10) -0.0021(8) 0.0039(8) -0.0032(10)
N5 0.0280(12) 0.0286(11) 0.0307(9) -0.0045(7) 0.0065(8) 0.0027(10)
N6 0.0326(13) 0.0456(14) 0.0406(11) -0.0167(11) 0.0134(9) -0.0135(12)
C1 0.0221(13) 0.0257(12) 0.0208(10) 0.0000(8) 0.0008(8) -0.0023(11)
C2 0.0347(16) 0.0278(14) 0.0397(14) 0.0045(11) -0.0045(12) -0.0086(12)
C3 0.0331(17) 0.0286(14) 0.0558(18) -0.0050(12) -0.0019(13) 0.0056(13)
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 0.0130
0 0 -1 0.0220
0 -2 -1 0.0600
0 3 -1 0.0260
-1 0 0 0.1050
1 1 1 0.1070
1 -1 1 0.1090
0 -2 1 0.0610
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 107.30(19)
C1 N1 C2 130.1(2)
N2 N1 C2 122.5(2)
N3 N2 N1 106.88(18)
N2 N3 N4 110.70(18)
C1 N4 N3 104.9(2)
N6 N5 C1 116.18(18)
N6 N5 C3 118.0(2)
C1 N5 C3 120.63(19)
O2 N6 O1 127.0(2)
O2 N6 N5 117.2(2)
O1 N6 N5 115.8(2)
N4 C1 N1 110.2(2)
N4 C1 N5 125.9(2)
N1 C1 N5 123.7(2)
N1 C2 H2A 106(2)
N1 C2 H2B 111(2)
H2A C2 H2B 115(3)
N1 C2 H2C 110(2)
H2A C2 H2C 100(3)
H2B C2 H2C 115(3)
N5 C3 H3A 112(2)
N5 C3 H3B 110.5(19)
H3A C3 H3B 109(3)
N5 C3 H3C 107.4(18)
H3A C3 H3C 109(3)
H3B C3 H3C 108(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N6 1.221(3)
O2 N6 1.220(3)
N1 C1 1.336(3)
N1 N2 1.341(3)
N1 C2 1.457(3)
N2 N3 1.299(3)
N3 N4 1.359(3)
N4 C1 1.308(3)
N5 N6 1.390(3)
N5 C1 1.391(3)
N5 C3 1.460(3)
C2 H2A 0.99(4)
C2 H2B 0.91(3)
C2 H2C 0.91(4)
C3 H3A 0.95(4)
C3 H3B 0.94(3)
C3 H3C 0.93(3)
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 0.7(2)
C2 N1 N2 N3 -177.40(19)
N1 N2 N3 N4 -0.5(2)
N2 N3 N4 C1 0.1(2)
C1 N5 N6 O2 13.1(3)
C3 N5 N6 O2 167.8(2)
C1 N5 N6 O1 -168.8(2)
C3 N5 N6 O1 -14.0(3)
N3 N4 C1 N1 0.3(2)
N3 N4 C1 N5 174.19(18)
N2 N1 C1 N4 -0.6(2)
C2 N1 C1 N4 177.3(2)
N2 N1 C1 N5 -174.66(18)
C2 N1 C1 N5 3.2(3)
N6 N5 C1 N4 108.4(2)
C3 N5 C1 N4 -45.7(3)
N6 N5 C1 N1 -78.5(2)
C3 N5 C1 N1 127.4(2)
