data_publication_text
_publ_requested_journal          'J. Am. Chem. Soc.'
_publ_contact_author_name        'Prof. Dr. Thomas M.  Klapötke'
_publ_contact_author_address     
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
_publ_contact_author_email       tmk@cup.uni-muenchen.de
_publ_contact_author_phone       +49-89-2180-77491
loop_
_publ_author_name
_publ_author_address
'Dominik Dosch'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
'Marco Reichel'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
'Konstantin Karaghiosoff'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
'Thomas M. Klapötke'
;
Department of Chemistry
Ludwig Maximilian University
Butenandtstr. 5-13 (D)
81377 Munich
Germany
;
  
data_picopic1_1 
  
_audit_creation_method            'SHELXL-2018/1' 
_shelx_SHELXL_version_number      '2018/1' 
_chemical_name_systematic         '2,2'-oxybis(1,3,5-trinitrobenzene)' 
_chemical_name_common             'Hexanitro-DPE / Dipicrylether'
_chemical_melting_point           ? 
_chemical_formula_moiety          
'C12 H4 N6 O13'
_chemical_formula_sum 
'C12 H4 N6 O13' 
_chemical_formula_weight          440.21 
  
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' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            4 
_space_group_name_H-M_alt         'P 21' 
_space_group_name_Hall            'P 2yb' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    8.0043(3) 
_cell_length_b                    8.7613(3) 
_cell_length_c                    11.7424(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  105.700(4) 
_cell_angle_gamma                 90 
_cell_volume                      792.75(5) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     143(2) 
_cell_measurement_reflns_used     4052 
_cell_measurement_theta_min       4.2430 
_cell_measurement_theta_max       31.4400 
  
_exptl_crystal_description        'cube' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_density_meas       . 
_exptl_crystal_density_method     . 
_exptl_crystal_density_diffrn     1.844 
_exptl_crystal_F_000              444 

_exptl_crystal_size_max           0.4
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.05 
_exptl_absorpt_coefficient_mu     0.172 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.91522 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_diffrn_ambient_temperature       143(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'fine-focus sealed X-ray tube' 
_diffrn_measurement_device_type   'Xcalibur, Sapphire3' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  15.9809 
_diffrn_reflns_number             15900 
_diffrn_reflns_av_unetI/netI      0.0434 
_diffrn_reflns_av_R_equivalents   0.0393 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          3.521 
_diffrn_reflns_theta_max          30.504 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.998 
_diffrn_measured_fraction_theta_full  0.997 
_diffrn_reflns_Laue_measured_fraction_max    0.998 
_diffrn_reflns_Laue_measured_fraction_full   0.997 
_diffrn_reflns_point_group_measured_fraction_max   0.999 
_diffrn_reflns_point_group_measured_fraction_full  0.998 
_reflns_number_total              4833 
_reflns_number_gt                 4120 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.888 
_reflns_Friedel_fraction_max      1.000 
_reflns_Friedel_fraction_full     0.999 
  
_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. 
; 
  
_computing_data_collection        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' 
_computing_cell_refinement        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' 
_computing_data_reduction         'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-2018/1 (Sheldrick, 2018)' 
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0343P)²+0.0867P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      'direct' 
_atom_sites_solution_secondary    'difmap' 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.2(5) 
_chemical_absolute_configuration  unk 
_refine_ls_number_reflns          4833 
_refine_ls_number_parameters      280 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0498 
_refine_ls_R_factor_gt            0.0388 
_refine_ls_wR_factor_ref          0.0835 
_refine_ls_wR_factor_gt           0.0779 
_refine_ls_goodness_of_fit_ref    1.038 
_refine_ls_restrained_S_all       1.038 
_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_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.4981(3) 0.5699(2) 0.05035(18) 0.0375(5) Uani 1 1 d . . . . . 
N1 N 0.4387(3) 0.6926(3) 0.00925(19) 0.0227(4) Uani 1 1 d . . . . . 
C1 C 0.3842(3) 0.7986(3) 0.0890(2) 0.0173(5) Uani 1 1 d . . . . . 
N2 N 0.0154(3) 1.0594(3) 0.0752(2) 0.0247(5) Uani 1 1 d . . . . . 
C2 C 0.4774(3) 0.8077(3) 0.2071(2) 0.0163(4) Uani 1 1 d . . . . . 
O2 O 0.4169(3) 0.7316(2) -0.09347(16) 0.0316(5) Uani 1 1 d . . . . . 
N5 N 0.9695(3) 0.7086(2) 0.2868(2) 0.0211(4) Uani 1 1 d . . . . . 
O5 O -0.0292(3) 1.1447(3) 0.1440(2) 0.0368(5) Uani 1 1 d . . . . . 
C5 C 0.1816(3) 0.9791(3) 0.1183(2) 0.0176(5) Uani 1 1 d . . . . . 
O3 O 0.5917(3) 0.8172(2) 0.45530(18) 0.0359(5) Uani 1 1 d . . . . . 
N3 N 0.5070(3) 0.9246(2) 0.40543(18) 0.0208(4) Uani 1 1 d . . . . . 
C3 C 0.4196(3) 0.9110(3) 0.2782(2) 0.0159(4) Uani 1 1 d . . . . . 
C4 C 0.2716(3) 0.9968(3) 0.2359(2) 0.0181(5) Uani 1 1 d . . . . . 
H4 H 0.232702 1.065667 0.285742 0.022 Uiso 1 1 calc R U . . . 
N4 N 0.4006(2) 0.4714(2) 0.27861(18) 0.0168(4) Uani 1 1 d . . . . . 
O4 O 0.4856(3) 1.0439(2) 0.45346(16) 0.0296(4) Uani 1 1 d . . . . . 
C12 C 0.6704(3) 0.3321(3) 0.3373(2) 0.0157(4) Uani 1 1 d . . . . . 
H12 H 0.603543 0.246136 0.347490 0.019 Uiso 1 1 calc R U . . . 
O12 O 1.0882(2) 0.1664(2) 0.42417(16) 0.0249(4) Uani 1 1 d . . . . . 
O13 O 0.8340(3) 0.0597(2) 0.3852(2) 0.0318(5) Uani 1 1 d . . . . . 
C6 C 0.2357(3) 0.8840(3) 0.0427(2) 0.0186(5) Uani 1 1 d . . . . . 
H6 H 0.173674 0.876985 -0.038430 0.022 Uiso 1 1 calc R U . . . 
N6 N 0.9287(3) 0.1708(2) 0.39177(19) 0.0209(4) Uani 1 1 d . . . . . 
O6 O -0.0696(3) 1.0351(3) -0.0262(2) 0.0416(6) Uani 1 1 d . . . . . 
C10 C 0.9495(3) 0.4425(3) 0.3454(2) 0.0183(5) Uani 1 1 d . . . . . 
H10 H 1.072089 0.433816 0.362126 0.022 Uiso 1 1 calc R U . . . 
O10 O 0.9369(3) 0.7578(3) 0.18569(19) 0.0369(5) Uani 1 1 d . . . . . 
C7 C 0.5903(3) 0.4706(3) 0.3011(2) 0.0150(4) Uani 1 1 d . . . . . 
O7 O 0.6370(2) 0.7422(2) 0.24830(16) 0.0226(4) Uani 1 1 d . . . . . 
C9 C 0.8657(3) 0.5771(3) 0.3072(2) 0.0173(4) Uani 1 1 d . . . . . 
O9 O 0.3285(2) 0.5928(2) 0.28451(16) 0.0211(4) Uani 1 1 d . . . . . 
C8 C 0.6854(3) 0.5978(3) 0.2842(2) 0.0152(4) Uani 1 1 d . . . . . 
O8 O 0.3255(2) 0.3495(2) 0.25712(19) 0.0291(5) Uani 1 1 d . . . . . 
C11 C 0.8471(3) 0.3198(3) 0.3585(2) 0.0168(5) Uani 1 1 d . . . . . 
O11 O 1.0813(2) 0.7570(2) 0.37075(19) 0.0299(4) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
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 N1 1.221(3) . ? 
N1 O2 1.220(3) . ? 
N1 C1 1.467(3) . ? 
C1 C6 1.385(3) . ? 
C1 C2 1.388(3) . ? 
N2 O6 1.220(3) . ? 
N2 O5 1.223(3) . ? 
N2 C5 1.469(3) . ? 
C2 O7 1.364(3) . ? 
C2 C3 1.392(3) . ? 
N5 O11 1.214(3) . ? 
N5 O10 1.223(3) . ? 
N5 C9 1.477(3) . ? 
C5 C6 1.370(3) . ? 
C5 C4 1.382(3) . ? 
O3 N3 1.214(3) . ? 
N3 O4 1.221(3) . ? 
N3 C3 1.473(3) . ? 
C3 C4 1.377(3) . ? 
N4 O8 1.218(3) . ? 
N4 O9 1.221(3) . ? 
N4 C7 1.469(3) . ? 
C12 C11 1.372(3) . ? 
C12 C7 1.385(3) . ? 
O12 N6 1.230(3) . ? 
O13 N6 1.223(3) . ? 
N6 C11 1.465(3) . ? 
C10 C9 1.370(3) . ? 
C10 C11 1.386(3) . ? 
C7 C8 1.393(3) . ? 
O7 C8 1.356(3) . ? 
C9 C8 1.407(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 
O2 N1 O1 125.0(2) . . ? 
O2 N1 C1 117.8(2) . . ? 
O1 N1 C1 117.1(2) . . ? 
C6 C1 C2 122.2(2) . . ? 
C6 C1 N1 117.6(2) . . ? 
C2 C1 N1 120.2(2) . . ? 
O6 N2 O5 124.5(2) . . ? 
O6 N2 C5 117.8(2) . . ? 
O5 N2 C5 117.7(2) . . ? 
O7 C2 C1 121.9(2) . . ? 
O7 C2 C3 119.5(2) . . ? 
C1 C2 C3 117.4(2) . . ? 
O11 N5 O10 125.6(2) . . ? 
O11 N5 C9 117.7(2) . . ? 
O10 N5 C9 116.8(2) . . ? 
C6 C5 C4 123.0(2) . . ? 
C6 C5 N2 118.9(2) . . ? 
C4 C5 N2 118.0(2) . . ? 
O3 N3 O4 124.8(2) . . ? 
O3 N3 C3 118.4(2) . . ? 
O4 N3 C3 116.8(2) . . ? 
C4 C3 C2 122.1(2) . . ? 
C4 C3 N3 116.6(2) . . ? 
C2 C3 N3 121.1(2) . . ? 
C3 C4 C5 117.6(2) . . ? 
O8 N4 O9 124.12(19) . . ? 
O8 N4 C7 117.5(2) . . ? 
O9 N4 C7 118.4(2) . . ? 
C11 C12 C7 119.6(2) . . ? 
C5 C6 C1 117.5(2) . . ? 
O13 N6 O12 124.6(2) . . ? 
O13 N6 C11 117.95(19) . . ? 
O12 N6 C11 117.4(2) . . ? 
C9 C10 C11 116.9(2) . . ? 
C12 C7 C8 121.3(2) . . ? 
C12 C7 N4 115.4(2) . . ? 
C8 C7 N4 123.3(2) . . ? 
C8 O7 C2 131.64(19) . . ? 
C10 C9 C8 124.0(2) . . ? 
C10 C9 N5 118.5(2) . . ? 
C8 C9 N5 117.4(2) . . ? 
O7 C8 C7 132.0(2) . . ? 
O7 C8 C9 111.8(2) . . ? 
C7 C8 C9 116.2(2) . . ? 
C12 C11 C10 122.0(2) . . ? 
C12 C11 N6 118.8(2) . . ? 
C10 C11 N6 119.1(2) . . ? 
  
_refine_diff_density_max    0.297 
_refine_diff_density_min   -0.222 
_refine_diff_density_rms    0.050 
  
  
  
