#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:41:26 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/11/7041100.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_7041100
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 H4 N6 O7'
_chemical_formula_sum            'C4 H4 N6 O7'
_chemical_formula_weight         248.13
_chemical_name_common            '4,4,4-trinitrobutanoyl azide'
_chemical_name_systematic        '4,4,4-trinitrobutanoyl azide'
_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
;
'Mon Sep 23 14:13:39 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                70.713(8)
_cell_angle_beta                 80.100(7)
_cell_angle_gamma                81.601(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4160(5)
_cell_length_b                   7.5385(6)
_cell_length_c                   9.0347(8)
_cell_measurement_reflns_used    1754
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.2160
_cell_measurement_theta_min      5.0870
_cell_volume                     467.47(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -57.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00  -39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   69.0000  -42.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000   90.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932 -179.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega   25.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
  8 omega   -3.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000  120.0000 92

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0721548000
_diffrn_orient_matrix_UB_12      -0.0725734000
_diffrn_orient_matrix_UB_13      0.0213489000
_diffrn_orient_matrix_UB_21      -0.0616298000
_diffrn_orient_matrix_UB_22      -0.0540109000
_diffrn_orient_matrix_UB_23      0.0618416000
_diffrn_orient_matrix_UB_31      -0.0225786000
_diffrn_orient_matrix_UB_32      -0.0429600000
_diffrn_orient_matrix_UB_33      -0.0525528000
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4352
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.20
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95454
_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    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         1909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0309
_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)+(0.0326P)²+0.1573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                1653
_reflns_number_total             1909
_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_original_cell_volume        467.47(6)
_cod_database_code               7041100
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
H1 H 0.378(2) 0.413(2) 0.1326(18) 0.016(4) Uiso 1 1 d
H2 H 0.216(2) 0.575(2) 0.087(2) 0.029(4) Uiso 1 1 d
H3 H 0.381(2) 0.480(3) 0.371(2) 0.031(5) Uiso 1 1 d
H4 H 0.227(2) 0.636(2) 0.330(2) 0.022(4) Uiso 1 1 d
C1 C 0.13830(18) 0.32995(19) 0.25378(16) 0.0162(3) Uani 1 1 d
C2 C 0.27179(18) 0.4782(2) 0.17659(17) 0.0172(3) Uani 1 1 d
C3 C 0.3282(2) 0.5701(2) 0.28695(18) 0.0211(3) Uani 1 1 d
C4 C 0.46565(17) 0.70870(19) 0.19632(17) 0.0172(3) Uani 1 1 d
N1 N 0.12868(14) 0.21194(16) 0.14658(14) 0.0166(3) Uani 1 1 d
N2 N 0.19272(17) 0.19228(16) 0.40896(14) 0.0208(3) Uani 1 1 d
N3 N -0.05937(15) 0.40911(17) 0.29229(14) 0.0190(3) Uani 1 1 d
N4 N 0.53102(16) 0.78319(17) 0.29878(14) 0.0208(3) Uani 1 1 d
N5 N 0.64411(16) 0.90474(17) 0.22376(14) 0.0208(3) Uani 1 1 d
N6 N 0.74495(19) 1.0116(2) 0.17012(16) 0.0292(3) Uani 1 1 d
O1 O 0.09088(13) 0.30344(14) 0.01533(12) 0.0217(2) Uani 1 1 d
O2 O 0.15949(13) 0.04165(13) 0.19888(12) 0.0217(2) Uani 1 1 d
O3 O 0.35386(14) 0.13098(15) 0.40455(13) 0.0288(3) Uani 1 1 d
O4 O 0.07365(15) 0.15714(15) 0.52257(12) 0.0286(3) Uani 1 1 d
O5 O -0.18229(14) 0.32850(17) 0.27729(14) 0.0318(3) Uani 1 1 d
O6 O -0.07630(13) 0.54618(15) 0.33707(13) 0.0245(3) Uani 1 1 d
O7 O 0.51209(13) 0.75092(14) 0.05546(12) 0.0224(2) Uani 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'
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'
H H 0.0000 0.0000 '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 N2 112.36(11)
C2 C1 N3 114.40(11)
N2 C1 N3 105.93(10)
C2 C1 N1 111.23(11)
N2 C1 N1 106.68(10)
N3 C1 N1 105.68(9)
C1 C2 C3 115.36(12)
C1 C2 H1 104.8(9)
C3 C2 H1 109.9(9)
C1 C2 H2 107.7(9)
C3 C2 H2 110.7(10)
H1 C2 H2 107.9(13)
C4 C3 C2 109.68(12)
C4 C3 H3 108.5(11)
C2 C3 H3 111.5(11)
C4 C3 H4 107.6(10)
C2 C3 H4 111.6(10)
H3 C3 H4 107.7(15)
O7 C4 N4 124.90(12)
O7 C4 C3 124.58(12)
N4 C4 C3 110.52(12)
O2 N1 O1 127.23(12)
O2 N1 C1 118.24(11)
O1 N1 C1 114.53(11)
O3 N2 O4 127.31(13)
O3 N2 C1 115.02(12)
O4 N2 C1 117.66(12)
O6 N3 O5 126.83(12)
O6 N3 C1 115.55(10)
O5 N3 C1 117.61(11)
N5 N4 C4 111.55(12)
N6 N5 N4 174.18(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5120(18)
C1 N2 1.5220(18)
C1 N3 1.5272(17)
C1 N1 1.5317(17)
C2 C3 1.5274(19)
C2 H1 0.966(16)
C2 H2 0.998(18)
C3 C4 1.5036(19)
C3 H3 0.939(19)
C3 H4 0.941(17)
C4 O7 1.2055(17)
C4 N4 1.4088(17)
N1 O2 1.2142(15)
N1 O1 1.2158(15)
N2 O3 1.2156(16)
N2 O4 1.2168(16)
N3 O6 1.2116(15)
N3 O5 1.2155(15)
N4 N5 1.2732(17)
N5 N6 1.1119(17)
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
N2 C1 C2 C3 -45.86(17)
N3 C1 C2 C3 74.97(15)
N1 C1 C2 C3 -165.38(12)
C1 C2 C3 C4 177.97(12)
C2 C3 C4 O7 5.5(2)
C2 C3 C4 N4 -175.05(12)
C2 C1 N1 O2 124.25(12)
N2 C1 N1 O2 1.41(15)
N3 C1 N1 O2 -111.03(12)
C2 C1 N1 O1 -55.37(14)
N2 C1 N1 O1 -178.22(10)
N3 C1 N1 O1 69.34(13)
C2 C1 N2 O3 -46.51(16)
N3 C1 N2 O3 -172.10(10)
N1 C1 N2 O3 75.63(13)
C2 C1 N2 O4 132.76(12)
N3 C1 N2 O4 7.17(15)
N1 C1 N2 O4 -105.10(12)
C2 C1 N3 O6 -37.19(16)
N2 C1 N3 O6 87.13(13)
N1 C1 N3 O6 -159.90(11)
C2 C1 N3 O5 143.73(13)
N2 C1 N3 O5 -91.95(14)
N1 C1 N3 O5 21.02(16)
O7 C4 N4 N5 1.2(2)
C3 C4 N4 N5 -178.28(12)
loop_
_iucr_refine_instructions_details
;
TITL ix434 in P-1
CELL  0.71073   7.4160   7.5385   9.0347   70.713   80.100   81.601
ZERR     2.00   0.0005   0.0006   0.0008    0.008    0.007    0.006
LATT   1
SFAC  C    N    O    H
UNIT  8    12   14   8
MERG   2
SHEL 0.8 1000
FMAP   2
PLAN   20
ACTA
HTAB
BOND   $H
CONF
L.S.  10
TEMP  -173.00
WGHT    0.032600    0.157300
FVAR      13.02480
H1    4    0.378456    0.412910    0.132606    11.00000    0.01611
H2    4    0.216371    0.575480    0.087014    11.00000    0.02855
H3    4    0.381264    0.479977    0.371392    11.00000    0.03111
H4    4    0.226928    0.636447    0.330160    11.00000    0.02231
MOLE    1
C1    1    0.138296    0.329955    0.253781    11.00000    0.01622    0.01922 =
         0.01435   -0.00675   -0.00387    0.00014
C2    1    0.271789    0.478193    0.176592    11.00000    0.01586    0.02168 =
         0.01593   -0.00800   -0.00144   -0.00342
C3    1    0.328188    0.570067    0.286947    11.00000    0.02230    0.02603 =
         0.01759   -0.00930   -0.00215   -0.00565
C4    1    0.465654    0.708695    0.196317    11.00000    0.01480    0.01849 =
         0.02074   -0.00962   -0.00455    0.00166
N1    2    0.128677    0.211935    0.146584    11.00000    0.01327    0.02101 =
         0.01776   -0.00833   -0.00258   -0.00232
N2    2    0.192721    0.192281    0.408960    11.00000    0.02834    0.01755 =
         0.01937   -0.00665   -0.00793   -0.00327
N3    2   -0.059372    0.409112    0.292287    11.00000    0.01670    0.02211 =
         0.01865   -0.00777   -0.00095   -0.00153
N4    2    0.531024    0.783188    0.298782    11.00000    0.02121    0.02328 =
         0.02117   -0.00906   -0.00463   -0.00525
N5    2    0.644109    0.904736    0.223762    11.00000    0.02066    0.02306 =
         0.02233   -0.00939   -0.00869   -0.00111
N6    2    0.744947    1.011574    0.170118    11.00000    0.03138    0.03220 =
         0.02895   -0.01083   -0.00892   -0.01021
O1    3    0.090880    0.303439    0.015325    11.00000    0.02377    0.02536 =
         0.01742   -0.00663   -0.00864   -0.00018
O2    3    0.159487    0.041645    0.198883    11.00000    0.02548    0.01692 =
         0.02381   -0.00723   -0.00396   -0.00268
O3    3    0.353859    0.130982    0.404548    11.00000    0.02800    0.02776 =
         0.03355   -0.01083   -0.01651    0.00563
O4    3    0.073653    0.157137    0.522574    11.00000    0.04113    0.02647 =
         0.01593   -0.00388    0.00129   -0.00887
O5    3   -0.182291    0.328497    0.277286    11.00000    0.01736    0.03952 =
         0.04690   -0.02430    0.00056   -0.00914
O6    3   -0.076299    0.546178    0.337069    11.00000    0.02150    0.02646 =
         0.02976   -0.01642   -0.00295    0.00153
O7    3    0.512094    0.750919    0.055462    11.00000    0.02235    0.02771 =
         0.02016   -0.01068   -0.00009   -0.00730
HKLF    4
 
REM  ix434 in P-1
REM R1 =  0.0309 for   1653 Fo > 4sig(Fo)  and  0.0384 for all   1909 data
REM    170 parameters refined using      0 restraints
 
END
 
WGHT      0.0326      0.1573
REM Highest difference peak  0.301,  deepest hole -0.217,  1-sigma level  0.044
Q1    1   0.2034  0.4062  0.2213  11.00000  0.05    0.30
Q2    1   0.3172  0.5034  0.2384  11.00000  0.05    0.26
Q3    1   0.1618  0.2829  0.3266  11.00000  0.05    0.26
Q4    1   0.3963  0.6451  0.2460  11.00000  0.05    0.25
Q5    1   0.0529  0.3613  0.2710  11.00000  0.05    0.23
Q6    1   0.1351  0.2771  0.2066  11.00000  0.05    0.21
Q7    1   0.4921  0.7603  0.2430  11.00000  0.05    0.17
Q8    1   0.0620  0.4407  0.0108  11.00000  0.05    0.15
Q9    1  -0.0042  0.3885  0.0689  11.00000  0.05    0.15
Q10   1   0.2728  0.2035  0.4175  11.00000  0.05    0.14
Q11   1  -0.1146  0.6638  0.4163  11.00000  0.05    0.14
Q12   1   0.4928  0.7462  0.4200  11.00000  0.05    0.14
Q13   1   0.0845  0.1690  0.0196  11.00000  0.05    0.14
Q14   1   0.5277  0.6008  0.0714  11.00000  0.05    0.13
Q15   1   0.4090  0.2192  0.3298  11.00000  0.05    0.13
Q16   1   0.0624 -0.0138  0.3214  11.00000  0.05    0.13
Q17   1   0.4439  0.4016  0.4011  11.00000  0.05    0.13
Q18   1   0.5381  0.6816  0.1393  11.00000  0.05    0.13
Q19   1   0.0173  0.5606  0.2388  11.00000  0.05    0.13
Q20   1   0.8068  1.1141  0.0901  11.00000  0.05    0.12
;
