data_manuscript

_publ_contact_author_name       'Thomas Reith'
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universitaet
Butenandtstrasse 5-13 (Haus D)
D-81377 Muenchen
Bundesrepublik Deutschland
;

_publ_author_name
;
Reith, Thomas

Klapoetke, Thomas M.
;
_publ_author_address
;
Reith, Thomas
Department Chemie
Ludwig-Maximilians Universitaet
Butenandtstrasse 5-13 (Haus D)
D-81377 Muenchen
Bundesrepublik Deutschland

Klapoetke, Thomas M.
Department Chemie
Ludwig-Maximilians Universitaet
Butenandtstrasse 5-13 (Haus D)
D-81377 Muenchen
Bundesrepublik Deutschland
;
# start Validation Reply Form
_vrf_PLAT430_manuscript
;
PROBLEM: Short Inter D...A Contact  O1       ..O2               2.78 Ang.  
RESPONSE: Disordered nitro group
;
_vrf_PLAT213_manuscript
;
PROBLEM: Atom O4              has ADP max/min Ratio .....        3.1 prolat
RESPONSE: Disordered nitro group
;
_vrf_PLAT242_manuscript
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         N6 Check 
RESPONSE: Disordered nitro group
;
# end Validation Reply Form

_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  ?
_publ_section_title
;
;

_publ_section_abstract  ?
_publ_section_comment   ?

_audit_author_name                'Thomas Reith'
_audit_block_code                 ?
_audit_creation_method            SHELXL-97
_audit_creation_date
;
'Thu Oct 13 08:37:40 2016'
;

_audit_update_record              ?

_chemical_name_systematic         
'1-(2,2,2-trinitroethyl)-1H-1,2,3-triazole-4,5-dicarbonitrile'
_chemical_compound_source         ?
_chemical_name_common             
'1-(2,2,2-trinitroethyl)-1H-1,2,3-triazole-4,5-dicarbonitrile'
_chemical_formula_moiety          
'C6 H2 N8 O6'
_chemical_formula_sum
 'C6 H2 N8 O6'
_chemical_formula_weight          282.130

_diffrn_ambient_temperature       173(2)
_diffrn_source_type               'Spellman generator'
_diffrn_source_power              ?
_diffrn_source_voltage            50 # kV
_diffrn_source_current            40 # mA
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_collimation     0.5
_diffrn_measurement_device        'CCD camera on κ-goniostat'
_diffrn_measurement_device_type   'KappaCCD'
_diffrn_measurement_method        'omega-scan'
_diffrn_radiation_type 		  'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number             8407
_diffrn_reflns_av_R_equivalents   0.0463
_diffrn_reflns_av_sigmaI/netI     0.0470
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          4.29
_diffrn_reflns_theta_max          26.36
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              26.36
_diffrn_measured_fraction_theta_full   0.995
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_number_total              2221
_reflns_number_gt                 1517
_reflns_threshold_expression      >2σ(I)

_diffrn_orient_matrix_UB_11      -0.0283453000
_diffrn_orient_matrix_UB_12       0.0275837000
_diffrn_orient_matrix_UB_13      -0.0612533000
_diffrn_orient_matrix_UB_21       0.0561410000
_diffrn_orient_matrix_UB_22       0.0415565000
_diffrn_orient_matrix_UB_23       0.0067927000
_diffrn_orient_matrix_UB_31       0.0270568000
_diffrn_orient_matrix_UB_32      -0.0571455000
_diffrn_orient_matrix_UB_33      -0.0246615000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00  -48.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -59.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   66.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   75.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega  -27.00  104.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932    0.0000  -60.0000 131

;
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_symmetry_Int_Tables_number       14
_symmetry_space_group_name_Hall   '-P 2yn'

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_
 _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'

_cell_length_a                    10.933(7)
_cell_length_b                    9.353(5)
_cell_length_c                    11.274(9)
_cell_angle_alpha                 90.000
_cell_angle_beta                  108.644(8)
_cell_angle_gamma                 90.000
_cell_volume                      1092.3(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used   1422
_cell_measurement_theta_min     4.5010
_cell_measurement_theta_max     27.4650
_cell_special_details             ?

_exptl_crystal_description        'needle'
_exptl_crystal_colour             'colorless'
_exptl_crystal_size_max           0.37
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.7156
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              568
_exptl_absorpt_coefficient_mu     0.155
_exptl_absorpt_correction_type            'multi-scan'
_exptl_absorpt_correction_T_min                   0.95970
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    0.367
_refine_diff_density_min   -0.321
_refine_diff_density_rms    0.047

_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution     'SIR-97'
_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
?

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0359P)²+0.4218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_extinction_expression  ?
_refine_ls_abs_structure_details  ?
_refine_ls_abs_structure_Flack    ?
_refine_ls_number_reflns          2221
_refine_ls_number_parameters      189
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0773
_refine_ls_R_factor_gt            0.0453
_refine_ls_wR_factor_ref          0.1064
_refine_ls_wR_factor_gt           0.0923
_refine_ls_goodness_of_fit_ref    1.023
_refine_ls_restrained_S_all       1.023
_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 1.19474(19) 0.36574(19) 0.2651(2) 0.0648(7) Uani 1 1 d . . .
N5 N 0.8798(2) 0.4725(2) 0.5367(2) 0.0453(6) Uani 1 1 d . . .
N1 N 0.85242(15) 0.21745(18) 0.30067(16) 0.0246(4) Uani 1 1 d . . .
N8 N 1.0549(2) 0.0266(2) 0.2665(2) 0.0418(6) Uani 1 1 d . . .
O5 O 1.0076(2) 0.0149(2) 0.1547(2) 0.0614(6) Uani 1 1 d . . .
O2 O 1.24799(18) 0.15562(19) 0.2247(2) 0.0568(6) Uani 1 1 d . . .
N3 N 0.68942(17) 0.0795(2) 0.27757(19) 0.0380(5) Uani 1 1 d . . .
C5 C 0.96317(19) 0.2740(2) 0.2701(2) 0.0236(5) Uani 1 1 d . . .
C4 C 0.8436(2) 0.3802(2) 0.4692(2) 0.0289(5) Uani 1 1 d . . .
O6 O 1.0799(2) -0.0675(2) 0.3440(2) 0.0722(7) Uani 1 1 d . . .
N6 N 1.18604(18) 0.2381(2) 0.26246(18) 0.0339(5) Uani 1 1 d . . .
C1 C 0.79661(18) 0.2652(2) 0.38476(19) 0.0237(5) Uani 1 1 d . . .
O3 O 1.07240(16) 0.1802(2) 0.51524(15) 0.0512(5) Uani 1 1 d . . .
N2 N 0.78596(18) 0.1055(2) 0.23652(18) 0.0367(5) Uani 1 1 d . . .
O4 O 1.25803(18) 0.1601(4) 0.49272(19) 0.0994(10) Uani 1 1 d . . .
C6 C 1.0816(2) 0.1792(2) 0.3126(2) 0.0272(5) Uani 1 1 d . . .
C2 C 0.69282(19) 0.1768(2) 0.3684(2) 0.0275(5) Uani 1 1 d . . .
N7 N 1.14351(18) 0.1731(2) 0.45386(18) 0.0420(5) Uani 1 1 d . . .
C3 C 0.6004(2) 0.1784(3) 0.4349(2) 0.0353(5) Uani 1 1 d . . .
N4 N 0.5304(2) 0.1806(3) 0.4902(2) 0.0532(6) Uani 1 1 d . . .
H1 H 0.9847(18) 0.364(2) 0.3084(19) 0.021(5) Uiso 1 1 d . . .
H2 H 0.942(2) 0.279(2) 0.183(2) 0.028(6) Uiso 1 1 d . . .


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 N6 1.197(3) . ?
N5 C4 1.135(3) . ?
N1 N2 1.346(2) . ?
N1 C1 1.357(2) . ?
N1 C5 1.460(2) . ?
N8 O5 1.205(3) . ?
N8 O6 1.208(3) . ?
N8 C6 1.516(3) . ?
O2 N6 1.192(2) . ?
N3 N2 1.304(2) . ?
N3 C2 1.362(3) . ?
C5 C6 1.515(3) . ?
C5 H1 0.94(2) . ?
C5 H2 0.94(2) . ?
C4 C1 1.419(3) . ?
N6 C6 1.530(3) . ?
C1 C2 1.368(3) . ?
O3 N7 1.196(2) . ?
O4 N7 1.193(3) . ?
C6 N7 1.519(3) . ?
C2 C3 1.438(3) . ?
C3 N4 1.131(3) . ?

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
N2 N1 C1 110.22(16) . . ?
N2 N1 C5 120.08(16) . . ?
C1 N1 C5 129.62(17) . . ?
O5 N8 O6 127.8(2) . . ?
O5 N8 C6 114.6(2) . . ?
O6 N8 C6 117.6(2) . . ?
N2 N3 C2 108.20(17) . . ?
N1 C5 C6 113.72(18) . . ?
N1 C5 H1 108.7(12) . . ?
C6 C5 H1 108.4(12) . . ?
N1 C5 H2 108.9(13) . . ?
C6 C5 H2 105.0(13) . . ?
H1 C5 H2 112.1(19) . . ?
N5 C4 C1 179.2(2) . . ?
O2 N6 O1 127.23(19) . . ?
O2 N6 C6 118.43(18) . . ?
O1 N6 C6 114.33(17) . . ?
N1 C1 C2 104.23(18) . . ?
N1 C1 C4 124.81(18) . . ?
C2 C1 C4 130.95(18) . . ?
N3 N2 N1 108.26(17) . . ?
C5 C6 N8 113.05(18) . . ?
C5 C6 N7 113.79(17) . . ?
N8 C6 N7 107.23(19) . . ?
C5 C6 N6 109.62(17) . . ?
N8 C6 N6 107.27(16) . . ?
N7 C6 N6 105.41(17) . . ?
N3 C2 C1 109.10(17) . . ?
N3 C2 C3 122.96(19) . . ?
C1 C2 C3 127.9(2) . . ?
O4 N7 O3 126.4(2) . . ?
O4 N7 C6 116.90(18) . . ?
O3 N7 C6 116.73(18) . . ?
N4 C3 C2 178.0(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
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
N2 N1 C5 C6 -73.3(3) . . . . ?
C1 N1 C5 C6 110.3(2) . . . . ?
N2 N1 C1 C2 -0.1(2) . . . . ?
C5 N1 C1 C2 176.6(2) . . . . ?
N2 N1 C1 C4 178.8(2) . . . . ?
C5 N1 C1 C4 -4.6(3) . . . . ?
C2 N3 N2 N1 0.6(2) . . . . ?
C1 N1 N2 N3 -0.3(2) . . . . ?
C5 N1 N2 N3 -177.33(18) . . . . ?
N1 C5 C6 N8 53.5(2) . . . . ?
N1 C5 C6 N7 -69.2(2) . . . . ?
N1 C5 C6 N6 173.10(17) . . . . ?
O5 N8 C6 C5 55.2(2) . . . . ?
O6 N8 C6 C5 -123.2(2) . . . . ?
O5 N8 C6 N7 -178.62(18) . . . . ?
O6 N8 C6 N7 3.0(2) . . . . ?
O5 N8 C6 N6 -65.8(2) . . . . ?
O6 N8 C6 N6 115.8(2) . . . . ?
O2 N6 C6 C5 -139.7(2) . . . . ?
O1 N6 C6 C5 39.6(3) . . . . ?
O2 N6 C6 N8 -16.6(3) . . . . ?
O1 N6 C6 N8 162.7(2) . . . . ?
O2 N6 C6 N7 97.5(2) . . . . ?
O1 N6 C6 N7 -83.2(2) . . . . ?
N2 N3 C2 C1 -0.7(3) . . . . ?
N2 N3 C2 C3 -179.5(2) . . . . ?
N1 C1 C2 N3 0.4(2) . . . . ?
C4 C1 C2 N3 -178.3(2) . . . . ?
N1 C1 C2 C3 179.2(2) . . . . ?
C4 C1 C2 C3 0.4(4) . . . . ?
C5 C6 N7 O4 -146.9(3) . . . . ?
N8 C6 N7 O4 87.3(3) . . . . ?
N6 C6 N7 O4 -26.7(3) . . . . ?
C5 C6 N7 O3 33.9(3) . . . . ?
N8 C6 N7 O3 -91.9(2) . . . . ?
N6 C6 N7 O3 154.0(2) . . . . ?

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
? ? ? ? ? ? ? ?

_geom_special_details         ?


