#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:41:26 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/11/7041101.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_7041101
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         'C3 H7 N4 O6, Cl, H2 O '
_chemical_formula_sum            'C3 H9 Cl N4 O7'
_chemical_formula_weight         248.579
_chemical_name_common            '3,3,3-Trinitropropan-1-aminium chloride'
_chemical_name_systematic        '3,3,3-Trinitropropan-1-aminium chloride'
_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 Oct 28 12:30:23 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                90.393(8)
_cell_angle_beta                 98.800(8)
_cell_angle_gamma                114.135(9)
_cell_formula_units_Z            2
_cell_length_a                   6.7434(6)
_cell_length_b                   7.8045(8)
_cell_length_c                   10.0663(10)
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7410
_cell_measurement_theta_min      4.2320
_cell_volume                     476.36(9)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00   40.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994    0.0000  -30.0000 139

#__ type_ start__ end____ width___ exp.time_
  2 omega -109.00  -81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00    3.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -77.0000  150.0000 104

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -57.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00  106.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega  -18.00   75.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000    0.0000 93

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0085459000
_diffrn_orient_matrix_UB_12      -0.0547512000
_diffrn_orient_matrix_UB_13      -0.0535624000
_diffrn_orient_matrix_UB_21      0.0642641000
_diffrn_orient_matrix_UB_22      0.0835415000
_diffrn_orient_matrix_UB_23      -0.0282716000
_diffrn_orient_matrix_UB_31      0.0973689000
_diffrn_orient_matrix_UB_32      -0.0005522000
_diffrn_orient_matrix_UB_33      0.0380276000
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4182
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         4.23
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99227
_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    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0277P)²+0.0677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0680
_reflns_number_gt                2050
_reflns_number_total             2345
_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        476.36(8)
_cod_database_code               7041101
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 0.1836(2) 0.29184(18) 0.19817(13) 0.0107(2) Uani 1 1 d
C2 C 0.2982(2) 0.46249(18) 0.29732(13) 0.0123(3) Uani 1 1 d
C3 C 0.3490(2) 0.65312(19) 0.23769(14) 0.0145(3) Uani 1 1 d
N1 N 0.29443(17) 0.30799(16) 0.07510(11) 0.0128(2) Uani 1 1 d
N2 N 0.18772(17) 0.11592(16) 0.26322(11) 0.0127(2) Uani 1 1 d
N3 N -0.05680(17) 0.24732(17) 0.14381(11) 0.0137(2) Uani 1 1 d
N4 N 0.5263(2) 0.80023(17) 0.33582(12) 0.0148(2) Uani 1 1 d
O1 O 0.17780(16) 0.25777(15) -0.03528(10) 0.0200(2) Uani 1 1 d
O2 O 0.49491(15) 0.37057(15) 0.10031(10) 0.0191(2) Uani 1 1 d
O3 O 0.23223(15) 0.01033(14) 0.19699(10) 0.0175(2) Uani 1 1 d
O4 O 0.14564(16) 0.09981(14) 0.37720(9) 0.0179(2) Uani 1 1 d
O5 O -0.19097(15) 0.08411(14) 0.13798(10) 0.0190(2) Uani 1 1 d
O6 O -0.08880(16) 0.38336(15) 0.10743(11) 0.0216(2) Uani 1 1 d
O7 O 0.86744(17) 0.68378(16) 0.35744(11) 0.0185(2) Uani 1 1 d
Cl1 Cl 0.28825(5) 0.74933(4) 0.58756(3) 0.01430(9) Uani 1 1 d
H1 H 0.207(3) 0.446(2) 0.3659(16) 0.018(4) Uiso 1 1 d
H2 H 0.434(3) 0.454(2) 0.3372(16) 0.017(4) Uiso 1 1 d
H3 H 0.223(2) 0.683(2) 0.2231(15) 0.013(4) Uiso 1 1 d
H5 H 0.398(3) 0.653(2) 0.1537(17) 0.021(4) Uiso 1 1 d
H6 H 0.647(3) 0.779(3) 0.3452(17) 0.026(5) Uiso 1 1 d
H7 H 0.558(3) 0.914(3) 0.3078(17) 0.022(4) Uiso 1 1 d
H8 H 0.476(3) 0.796(3) 0.412(2) 0.030(5) Uiso 1 1 d
H9 H 0.976(3) 0.735(3) 0.417(2) 0.040(6) Uiso 1 1 d
H10 H 0.826(3) 0.570(3) 0.360(2) 0.041(6) 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'
Cl Cl 0.1484 0.1585 '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 114.45(10)
C2 C1 N1 112.98(10)
N3 C1 N1 105.91(9)
C2 C1 N2 110.60(10)
N3 C1 N2 106.71(10)
N1 C1 N2 105.60(10)
C1 C2 C3 115.77(11)
C1 C2 H1 106.9(10)
C3 C2 H1 110.8(10)
C1 C2 H2 104.0(10)
C3 C2 H2 110.1(10)
H1 C2 H2 108.9(13)
N4 C3 C2 107.55(11)
N4 C3 H3 108.4(9)
C2 C3 H3 112.5(9)
N4 C3 H5 109.8(10)
C2 C3 H5 110.1(10)
H3 C3 H5 108.5(13)
O1 N1 O2 127.28(11)
O1 N1 C1 118.20(10)
O2 N1 C1 114.52(10)
O3 N2 O4 127.65(12)
O3 N2 C1 117.24(11)
O4 N2 C1 115.11(10)
O6 N3 O5 127.96(11)
O6 N3 C1 113.90(11)
O5 N3 C1 118.11(11)
C3 N4 H6 109.3(12)
C3 N4 H7 111.3(11)
H6 N4 H7 108.3(16)
C3 N4 H8 107.7(12)
H6 N4 H8 112.4(16)
H7 N4 H8 107.8(16)
H9 O7 H10 108(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5071(17)
C1 N3 1.5213(16)
C1 N1 1.5221(16)
C1 N2 1.5337(16)
C2 C3 1.5328(18)
C2 H1 0.968(16)
C2 H2 0.970(16)
C3 N4 1.4913(17)
C3 H3 0.960(15)
C3 H5 0.954(17)
N1 O1 1.2171(14)
N1 O2 1.2182(14)
N2 O3 1.2123(14)
N2 O4 1.2187(14)
N3 O6 1.2151(15)
N3 O5 1.2185(15)
N4 H6 0.882(18)
N4 H7 0.882(19)
N4 H8 0.88(2)
O7 H9 0.82(2)
O7 H10 0.81(2)
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 -71.89(15)
N1 C1 C2 C3 49.43(15)
N2 C1 C2 C3 167.56(11)
C1 C2 C3 N4 -160.05(11)
C2 C1 N1 O1 -136.74(12)
N3 C1 N1 O1 -10.71(15)
N2 C1 N1 O1 102.25(12)
C2 C1 N1 O2 43.65(15)
N3 C1 N1 O2 169.69(10)
N2 C1 N1 O2 -77.35(13)
C2 C1 N2 O3 -136.09(11)
N3 C1 N2 O3 98.84(12)
N1 C1 N2 O3 -13.55(14)
C2 C1 N2 O4 43.71(14)
N3 C1 N2 O4 -81.35(12)
N1 C1 N2 O4 166.25(10)
C2 C1 N3 O6 46.80(15)
N1 C1 N3 O6 -78.33(13)
N2 C1 N3 O6 169.49(10)
C2 C1 N3 O5 -135.21(12)
N1 C1 N3 O5 99.66(12)
N2 C1 N3 O5 -12.52(15)
loop_
_iucr_refine_instructions_details
;
TITL ix504 in P-1
CELL  0.71073   6.7434   7.8045  10.0663   90.393   98.800  114.135
ZERR     2.00   0.0006   0.0008   0.0010    0.008    0.008    0.009
LATT   1
SFAC  C    H    N    O    CL
UNIT  6    18   8    14   2
MERG   2
OMIT     2  -1   1
SHEL  0.75 1000
FMAP   2
PLAN   20
ACTA
BOND   $H
CONF
L.S.  10
TEMP  -173.00
WGHT    0.027700    0.067700
FVAR      11.76519
C1    1    0.183637    0.291838    0.198166    11.00000    0.01082    0.01138 =
         0.01113    0.00186    0.00222    0.00574
C2    1    0.298166    0.462492    0.297323    11.00000    0.01443    0.00954 =
         0.01240    0.00024    0.00158    0.00466
C3    1    0.349004    0.653122    0.237691    11.00000    0.01929    0.01004 =
         0.01381    0.00030    0.00131    0.00634
N1    3    0.294426    0.307994    0.075103    11.00000    0.01579    0.01109 =
         0.01428    0.00136    0.00495    0.00755
N2    3    0.187719    0.115916    0.263217    11.00000    0.01174    0.00931 =
         0.01562    0.00061   -0.00011    0.00370
N3    3   -0.056804    0.247316    0.143815    11.00000    0.01041    0.01784 =
         0.01320    0.00003    0.00162    0.00635
N4    3    0.526326    0.800229    0.335816    11.00000    0.01757    0.00942 =
         0.01666    0.00082    0.00413    0.00452
O1    4    0.177802    0.257769   -0.035278    11.00000    0.02348    0.02108 =
         0.01154   -0.00348    0.00075    0.00621
O2    4    0.494913    0.370565    0.100306    11.00000    0.01226    0.02526 =
         0.02388    0.00645    0.00620    0.01064
O3    4    0.232229    0.010329    0.196987    11.00000    0.01976    0.01220 =
         0.02201   -0.00220    0.00177    0.00886
O4    4    0.145645    0.099805    0.377198    11.00000    0.02346    0.01525 =
         0.01386    0.00428    0.00460    0.00625
O5    4   -0.190967    0.084113    0.137977    11.00000    0.01302    0.01539 =
         0.02298   -0.00383    0.00139    0.00109
O6    4   -0.088802    0.383358    0.107429    11.00000    0.01702    0.02254 =
         0.02873    0.00765    0.00188    0.01223
O7    4    0.867442    0.683782    0.357439    11.00000    0.01747    0.01261 =
         0.02166   -0.00066   -0.00193    0.00445
CL1   5    0.288246    0.749330    0.587563    11.00000    0.01447    0.01251 =
         0.01533    0.00044    0.00138    0.00543
H1    2    0.207130    0.445943    0.365915    11.00000    0.01787
H2    2    0.434024    0.454273    0.337186    11.00000    0.01737
H3    2    0.223256    0.683192    0.223124    11.00000    0.01348
H5    2    0.398258    0.653049    0.153748    11.00000    0.02054
H6    2    0.646627    0.779419    0.345176    11.00000    0.02581
H7    2    0.558346    0.913807    0.307849    11.00000    0.02168
H8    2    0.476479    0.796117    0.412496    11.00000    0.03035
H9    2    0.976184    0.735226    0.416791    11.00000    0.04013
H10   2    0.826388    0.570276    0.359954    11.00000    0.04101
HKLF    4
 
REM  ix504 in P-1
REM R1 =  0.0287 for   2050 Fo > 4sig(Fo)  and  0.0355 for all   2345 data
REM    172 parameters refined using      0 restraints
 
END
 
WGHT      0.0277      0.0677
REM Highest difference peak  0.336,  deepest hole -0.292,  1-sigma level  0.057
Q1    1   0.3464  0.5598  0.2738  11.00000  0.05    0.34
Q2    1   0.1886  0.2214  0.2311  11.00000  0.05    0.32
Q3    1   0.2468  0.3742  0.2434  11.00000  0.05    0.31
Q4    1   0.2264  0.2952  0.1385  11.00000  0.05    0.31
Q5    1   0.0906  0.2761  0.1788  11.00000  0.05    0.27
Q6    1   0.2718  0.5984  0.5021  11.00000  0.05    0.21
Q7    1   0.3062  0.6792  0.6776  11.00000  0.05    0.21
Q8    1   0.0821 -0.0418  0.3641  11.00000  0.05    0.20
Q9    1   0.1671 -0.0433  0.1066  11.00000  0.05    0.19
Q10   1   1.1748  0.8836  0.3604  11.00000  0.05    0.19
Q11   1   0.0768  0.0139  0.0592  11.00000  0.05    0.18
Q12   1  -0.1953 -0.0183 -0.0152  11.00000  0.05    0.18
Q13   1   0.4182  0.9588  0.5121  11.00000  0.05    0.18
Q14   1   0.2850  0.0932  0.0508  11.00000  0.05    0.18
Q15   1   0.2487  0.8926  0.6413  11.00000  0.05    0.17
Q16   1   0.2481  0.0779  0.1356  11.00000  0.05    0.17
Q17   1   0.3532  0.5266  0.2027  11.00000  0.05    0.17
Q18   1   0.4957  0.6711  0.1471  11.00000  0.05    0.17
Q19   1   0.3897  0.3778  0.3798  11.00000  0.05    0.17
Q20   1   0.5242  0.5987  0.2168  11.00000  0.05    0.16
;
