#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:41:26 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/10/7041098.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_7041098
loop_
_publ_author_name
'Axthammer, Quirin J.'
'Klapötke, Thomas M'
'Krumm, Burkhard'
'Scharf, Regina'
'Unger, Cornelia C.'
_publ_section_title
;
 Convenient synthesis of energetic polynitro materials including
 (NO2)3CCH2CH2NH3-salts via Michael addition of trinitromethane.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              18909
_journal_page_last               18920
_journal_paper_doi               10.1039/c6dt03779h
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C4 H6 N4 O7'
_chemical_formula_sum            'C4 H6 N4 O7'
_chemical_formula_weight         222.11
_chemical_name_common            4,4,4-trinitrobutanamide
_chemical_name_systematic        4,4,4-trinitrobutanamide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Thu Jun 20 15:18:27 2013'
;
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-26 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                80.728(7)
_cell_angle_beta                 87.505(7)
_cell_angle_gamma                88.355(6)
_cell_formula_units_Z            2
_cell_length_a                   6.1081(5)
_cell_length_b                   7.5366(6)
_cell_length_c                   8.8543(7)
_cell_measurement_reflns_used    1595
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.2010
_cell_measurement_theta_min      4.7930
_cell_volume                     401.80(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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).
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   41.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994   57.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -97.00  -19.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -57.0000  120.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00  102.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
  5 omega  -24.00   74.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega  -16.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000 -120.0000 80

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      -0.0459895000
_diffrn_orient_matrix_UB_12      -0.0833300000
_diffrn_orient_matrix_UB_13      0.0331760000
_diffrn_orient_matrix_UB_21      0.0550389000
_diffrn_orient_matrix_UB_22      -0.0422974000
_diffrn_orient_matrix_UB_23      -0.0572952000
_diffrn_orient_matrix_UB_31      0.0915024000
_diffrn_orient_matrix_UB_32      -0.0191055000
_diffrn_orient_matrix_UB_33      0.0470663000
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3448
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         4.27
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0308
_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)+(0.0336P)²+0.0521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                1685
_reflns_number_total             1971
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c6dt03779h2.cif
_cod_data_source_block           manuscript
_cod_depositor_comments
'Adding full bibliography for 7041098--7041104.cif.'
_cod_database_code               7041098
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.60494(18) 0.69331(16) 0.23573(13) 0.0109(2) Uani 1 1 d
C2 C 0.74978(19) 0.55286(16) 0.32417(13) 0.0113(2) Uani 1 1 d
C3 C 0.7997(2) 0.38700(16) 0.24931(14) 0.0130(2) Uani 1 1 d
C4 C 0.89121(18) 0.23470(16) 0.36527(13) 0.0113(2) Uani 1 1 d
N1 N 0.57563(16) 0.86215(13) 0.31264(11) 0.0126(2) Uani 1 1 d
N2 N 0.37105(16) 0.63111(14) 0.21820(12) 0.0134(2) Uani 1 1 d
N3 N 0.70263(16) 0.75246(13) 0.07520(11) 0.0122(2) Uani 1 1 d
N4 N 1.01006(17) 0.10997(15) 0.30589(12) 0.0141(2) Uani 1 1 d
O1 O 0.63973(14) 0.84792(12) 0.44160(10) 0.0168(2) Uani 1 1 d
O2 O 0.49001(15) 0.99389(12) 0.23761(11) 0.0199(2) Uani 1 1 d
O3 O 0.25978(15) 0.72431(14) 0.12417(12) 0.0259(2) Uani 1 1 d
O4 O 0.31492(14) 0.49514(12) 0.30229(10) 0.0158(2) Uani 1 1 d
O5 O 0.66121(16) 0.65946(13) -0.01991(10) 0.0219(2) Uani 1 1 d
O6 O 0.82850(14) 0.87652(12) 0.05792(10) 0.0188(2) Uani 1 1 d
O7 O 0.84909(14) 0.22584(11) 0.50422(9) 0.0143(2) Uani 1 1 d
H1 H 0.880(2) 0.612(2) 0.3408(17) 0.017 Uiso 1 1 d
H2 H 0.673(2) 0.519(2) 0.4216(17) 0.017 Uiso 1 1 d
H3 H 0.670(2) 0.342(2) 0.2123(17) 0.017 Uiso 1 1 d
H4 H 0.905(2) 0.412(2) 0.1609(17) 0.017 Uiso 1 1 d
H5 H 1.040(2) 0.128(2) 0.2056(18) 0.017 Uiso 1 1 d
H6 H 1.066(2) 0.016(2) 0.3620(17) 0.017 Uiso 1 1 d
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 N3 110.49(9)
C2 C1 N2 114.15(10)
N3 C1 N2 107.07(9)
C2 C1 N1 112.09(9)
N3 C1 N1 107.44(9)
N2 C1 N1 105.19(9)
C1 C2 C3 115.16(10)
C1 C2 H1 106.1(9)
C3 C2 H1 111.7(9)
C1 C2 H2 105.1(8)
C3 C2 H2 110.0(9)
H1 C2 H2 108.3(13)
C4 C3 C2 110.38(10)
C4 C3 H3 106.3(9)
C2 C3 H3 111.8(9)
C4 C3 H4 109.2(8)
C2 C3 H4 112.1(9)
H3 C3 H4 106.9(12)
O7 C4 N4 123.15(11)
O7 C4 C3 121.47(10)
N4 C4 C3 115.32(10)
O1 N1 O2 127.55(11)
O1 N1 C1 115.79(9)
O2 N1 C1 116.65(10)
O4 N2 O3 126.61(11)
O4 N2 C1 116.27(9)
O3 N2 C1 117.09(10)
O6 N3 O5 126.50(10)
O6 N3 C1 117.14(10)
O5 N3 C1 116.01(10)
C4 N4 H5 118.4(10)
C4 N4 H6 122.5(10)
H5 N4 H6 119.0(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5020(16)
C1 N3 1.5206(15)
C1 N2 1.5382(15)
C1 N1 1.5396(15)
C2 C3 1.5240(17)
C2 H1 0.953(16)
C2 H2 0.963(15)
C3 C4 1.5223(16)
C3 H3 0.962(16)
C3 H4 0.988(15)
C4 O7 1.2375(14)
C4 N4 1.3320(15)
N1 O1 1.2106(13)
N1 O2 1.2201(13)
N2 O4 1.2141(13)
N2 O3 1.2173(13)
N3 O6 1.2140(13)
N3 O5 1.2179(14)
N4 H5 0.889(16)
N4 H6 0.868(16)
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
N3 C1 C2 C3 -56.06(13)
N2 C1 C2 C3 64.66(13)
N1 C1 C2 C3 -175.87(10)
C1 C2 C3 C4 -164.29(10)
C2 C3 C4 O7 25.44(16)
C2 C3 C4 N4 -157.30(11)
C2 C1 N1 O1 -11.60(14)
N3 C1 N1 O1 -133.17(10)
N2 C1 N1 O1 112.99(10)
C2 C1 N1 O2 168.78(10)
N3 C1 N1 O2 47.21(13)
N2 C1 N1 O2 -66.63(12)
C2 C1 N2 O4 15.22(14)
N3 C1 N2 O4 137.83(10)
N1 C1 N2 O4 -108.07(11)
C2 C1 N2 O3 -166.18(10)
N3 C1 N2 O3 -43.56(13)
N1 C1 N2 O3 70.54(12)
C2 C1 N3 O6 -88.99(12)
N2 C1 N3 O6 146.14(10)
N1 C1 N3 O6 33.57(13)
C2 C1 N3 O5 84.66(12)
N2 C1 N3 O5 -40.20(13)
N1 C1 N3 O5 -152.78(10)
loop_
_iucr_refine_instructions_details
;
TITL P-1 in P-1
CELL  0.71069   6.1081   7.5366   8.8543   80.728   87.505   88.355
ZERR     2.00   0.0005   0.0006   0.0007    0.007    0.007    0.006
LATT   1
SFAC  C    H    N    O
UNIT  8    12   8    14
MERG   2
OMIT    -2  -1   1
OMIT     2  -5   3
OMIT    -1   6   5
OMIT     0  -6   6
OMIT    -1   0   3
SHEL 0.75 1000
FMAP   2
PLAN   20
ACTA
HTAB    2.00000
BOND   $H
CONF
L.S.  10
TEMP  -173.00
WGHT    0.033600    0.052100
FVAR       0.39700
C1    1    0.604936    0.693313    0.235727    11.00000    0.01107    0.01013 =
         0.01143   -0.00122    0.00006   -0.00093
C2    1    0.749781    0.552864    0.324170    11.00000    0.01294    0.01027 =
         0.01049   -0.00055   -0.00228    0.00117
C3    1    0.799709    0.386998    0.249307    11.00000    0.01608    0.01093 =
         0.01196   -0.00201   -0.00252    0.00298
C4    1    0.891206    0.234698    0.365272    11.00000    0.00954    0.01051 =
         0.01387   -0.00132   -0.00148   -0.00120
N1    3    0.575634    0.862145    0.312644    11.00000    0.01149    0.01102 =
         0.01507   -0.00205    0.00109    0.00052
N2    3    0.371045    0.631106    0.218203    11.00000    0.01289    0.01298 =
         0.01477   -0.00343   -0.00154    0.00013
N3    3    0.702628    0.752456    0.075199    11.00000    0.01334    0.01073 =
         0.01163    0.00068   -0.00084    0.00215
N4    3    1.010063    0.109965    0.305885    11.00000    0.01820    0.01192 =
         0.01113   -0.00007    0.00052    0.00435
O1    4    0.639726    0.847920    0.441597    11.00000    0.01954    0.01771 =
         0.01442   -0.00557   -0.00279    0.00047
O2    4    0.490011    0.993886    0.237607    11.00000    0.02310    0.01277 =
         0.02278   -0.00076   -0.00243    0.00686
O3    4    0.259780    0.724306    0.124173    11.00000    0.01884    0.02280 =
         0.03381    0.00535   -0.01292    0.00091
O4    4    0.314924    0.495138    0.302288    11.00000    0.01662    0.01547 =
         0.01546   -0.00311    0.00247   -0.00473
O5    4    0.661210    0.659463   -0.019906    11.00000    0.03664    0.01722 =
         0.01274   -0.00457   -0.00131   -0.00343
O6    4    0.828501    0.876518    0.057922    11.00000    0.01741    0.02000 =
         0.01811   -0.00031    0.00110   -0.00604
O7    4    0.849088    0.225841    0.504224    11.00000    0.01778    0.01232 =
         0.01245   -0.00122   -0.00008    0.00183
H1    2    0.880183    0.612192    0.340790    11.00000   -1.20000
H2    2    0.673283    0.518958    0.421566    11.00000   -1.20000
H3    2    0.669729    0.342148    0.212279    11.00000   -1.20000
H4    2    0.904788    0.412029    0.160853    11.00000   -1.20000
H5    2    1.040369    0.127974    0.205553    11.00000   -1.20000
H6    2    1.065712    0.015768    0.361991    11.00000   -1.20000
HKLF    4
 
REM  P-1 in P-1
REM R1 =  0.0308 for   1685 Fo > 4sig(Fo)  and  0.0380 for all   1971 data
REM    154 parameters refined using      0 restraints
 
END
 
WGHT      0.0336      0.0521
REM Highest difference peak  0.388,  deepest hole -0.228,  1-sigma level  0.049
Q1    1   0.6439  0.7155  0.1568  11.00000  0.05    0.39
Q2    1   0.8568  0.3134  0.3007  11.00000  0.05    0.34
Q3    1   0.5031  0.6639  0.2320  11.00000  0.05    0.29
Q4    1   0.6721  0.6189  0.2761  11.00000  0.05    0.29
Q5    1   0.5939  0.7772  0.2641  11.00000  0.05    0.29
Q6    1   0.7770  0.4730  0.2755  11.00000  0.05    0.26
Q7    1   0.9856  0.2040  0.3267  11.00000  0.05    0.21
Q8    1   0.3807  0.7186  0.0876  11.00000  0.05    0.18
Q9    1   0.7166  0.2744  0.5368  11.00000  0.05    0.18
Q10   1   0.9477  0.8640 -0.0029  11.00000  0.05    0.17
Q11   1   0.5414  0.4299  0.4368  11.00000  0.05    0.16
Q12   1   0.6026  0.7362  0.0152  11.00000  0.05    0.15
Q13   1   0.7448  0.3662  0.2380  11.00000  0.05    0.15
Q14   1   0.8259  0.7757  0.5004  11.00000  0.05    0.15
Q15   1   0.4972  0.9259  0.1662  11.00000  0.05    0.15
Q16   1   0.5360  0.3598  0.2369  11.00000  0.05    0.15
Q17   1   0.5491  0.6259  0.0359  11.00000  0.05    0.14
Q18   1   0.5710  1.0721  0.4284  11.00000  0.05    0.14
Q19   1   0.7102  0.7411  0.4331  11.00000  0.05    0.14
Q20   1   0.6854  0.9973  0.3880  11.00000  0.05    0.14
;
