#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:41:26 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190216 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/10/7041099.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_7041099
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 H5 N3 O8'
_chemical_formula_sum            'C4 H5 N3 O8'
_chemical_formula_weight         223.11
_chemical_name_common            '4,4,4-trinitrobutanoic acid'
_chemical_name_systematic        '4,4,4-trinitrobutanoic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Mon Sep 23 17:48:24 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                90.00
_cell_angle_beta                 98.296(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1307(3)
_cell_length_b                   16.7082(8)
_cell_length_c                   8.5025(4)
_cell_measurement_reflns_used    1412
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6460
_cell_measurement_theta_min      4.8530
_cell_volume                     861.82(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00  -43.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega  -75.00   40.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994   19.0000  -90.0000 115

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00  -17.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -57.0000  -60.0000 79

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0780852000
_diffrn_orient_matrix_UB_12      0.0164800000
_diffrn_orient_matrix_UB_13      -0.0446212000
_diffrn_orient_matrix_UB_21      -0.0867299000
_diffrn_orient_matrix_UB_22      0.0128634000
_diffrn_orient_matrix_UB_23      -0.0589364000
_diffrn_orient_matrix_UB_31      -0.0047019000
_diffrn_orient_matrix_UB_32      0.0369902000
_diffrn_orient_matrix_UB_33      0.0406017000
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3513
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.15
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98893
_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    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_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     156
_refine_ls_number_reflns         1750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0306
_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)+(0.0314P)²+0.2537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                1484
_reflns_number_total             1750
_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_sg_symbol_H-M      'P 21/n'
_cod_database_code               7041099
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'
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 0.1899(2) 0.16038(8) 0.50446(15) 0.0160(3) Uani 1 1 d
C2 C 0.2605(2) 0.14469(8) 0.34510(15) 0.0162(3) Uani 1 1 d
C3 C 0.1759(2) 0.06656(8) 0.26509(16) 0.0182(3) Uani 1 1 d
C4 C 0.3177(2) 0.04059(8) 0.14329(15) 0.0171(3) Uani 1 1 d
N1 N -0.05798(17) 0.16668(7) 0.50386(13) 0.0193(3) Uani 1 1 d
N2 N 0.28918(19) 0.23884(7) 0.57637(15) 0.0248(3) Uani 1 1 d
N3 N 0.26837(18) 0.09570(7) 0.62807(13) 0.0205(3) Uani 1 1 d
O1 O -0.16326(15) 0.10905(6) 0.44817(12) 0.0263(2) Uani 1 1 d
O2 O -0.12968(17) 0.22714(6) 0.55766(13) 0.0310(3) Uani 1 1 d
O3 O 0.3042(2) 0.29303(6) 0.48502(14) 0.0372(3) Uani 1 1 d
O4 O 0.3451(2) 0.23968(8) 0.71904(13) 0.0440(3) Uani 1 1 d
O5 O 0.15010(17) 0.07972(6) 0.72603(12) 0.0297(3) Uani 1 1 d
O6 O 0.44714(17) 0.06761(8) 0.61692(14) 0.0394(3) Uani 1 1 d
O7 O 0.47767(15) 0.07841(6) 0.11543(11) 0.0224(2) Uani 1 1 d
O8 O 0.24985(16) -0.02702(6) 0.07489(12) 0.0223(2) Uani 1 1 d
H1 H 0.418(3) 0.1446(9) 0.3669(17) 0.019(4) Uiso 1 1 d
H2 H 0.215(2) 0.1894(9) 0.2827(17) 0.017(4) Uiso 1 1 d
H3 H 0.179(2) 0.0227(10) 0.3438(19) 0.023(4) Uiso 1 1 d
H4 H 0.026(3) 0.0708(9) 0.2123(19) 0.026(4) Uiso 1 1 d
H5 H 0.341(3) -0.0419(12) 0.012(2) 0.050(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 N1 115.21(11)
C2 C1 N2 111.02(10)
N1 C1 N2 106.29(10)
C2 C1 N3 113.06(10)
N1 C1 N3 105.35(9)
N2 C1 N3 105.16(10)
C1 C2 C3 115.26(11)
C1 C2 H1 103.9(9)
C3 C2 H1 110.7(9)
C1 C2 H2 105.7(9)
C3 C2 H2 112.1(9)
H1 C2 H2 108.7(13)
C4 C3 C2 111.03(11)
C4 C3 H3 107.1(9)
C2 C3 H3 111.0(9)
C4 C3 H4 107.9(9)
C2 C3 H4 112.6(9)
H3 C3 H4 106.9(12)
O7 C4 O8 125.02(12)
O7 C4 C3 122.96(12)
O8 C4 C3 112.01(11)
O1 N1 O2 127.10(11)
O1 N1 C1 114.82(10)
O2 N1 C1 118.07(11)
O3 N2 O4 126.83(13)
O3 N2 C1 116.61(12)
O4 N2 C1 116.56(12)
O6 N3 O5 127.47(12)
O6 N3 C1 114.68(11)
O5 N3 C1 117.83(11)
C4 O8 H5 109.4(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5038(17)
C1 N1 1.5228(16)
C1 N2 1.5346(17)
C1 N3 1.5354(17)
C2 C3 1.5279(18)
C2 H1 0.956(15)
C2 H2 0.935(15)
C3 C4 1.5088(18)
C3 H3 0.991(17)
C3 H4 0.966(16)
C4 O7 1.2181(16)
C4 O8 1.3106(16)
N1 O1 1.2165(14)
N1 O2 1.2170(15)
N2 O3 1.2052(16)
N2 O4 1.2121(16)
N3 O6 1.2085(15)
N3 O5 1.2104(14)
O8 H5 0.86(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
N1 C1 C2 C3 -60.82(15)
N2 C1 C2 C3 178.31(11)
N3 C1 C2 C3 60.41(15)
C1 C2 C3 C4 -158.38(11)
C2 C3 C4 O7 0.01(18)
C2 C3 C4 O8 179.04(11)
C2 C1 N1 O1 55.76(15)
N2 C1 N1 O1 179.17(11)
N3 C1 N1 O1 -69.56(13)
C2 C1 N1 O2 -124.27(13)
N2 C1 N1 O2 -0.86(15)
N3 C1 N1 O2 110.41(12)
C2 C1 N2 O3 36.70(16)
N1 C1 N2 O3 -89.29(13)
N3 C1 N2 O3 159.30(12)
C2 C1 N2 O4 -143.01(13)
N1 C1 N2 O4 91.00(14)
N3 C1 N2 O4 -20.40(15)
C2 C1 N3 O6 35.08(16)
N1 C1 N3 O6 161.73(11)
N2 C1 N3 O6 -86.20(14)
C2 C1 N3 O5 -146.38(12)
N1 C1 N3 O5 -19.73(15)
N2 C1 N3 O5 92.34(13)
loop_
_iucr_refine_instructions_details
;
TITL ix435 in P2(1)/n
CELL  0.71073   6.1307  16.7082   8.5025   90.000   98.296   90.000
ZERR     4.00   0.0003   0.0008   0.0004    0.000    0.004    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  16   20   12   32
MERG   2
SHEL 0.8 1000
FMAP   2
PLAN   20
ACTA
HTAB    2.00000
BOND   $H
CONF
L.S.  10
TEMP  -173.00
WGHT    0.031400    0.253700
FVAR       9.65320
C1    1    0.189940    0.160376    0.504463    11.00000    0.01530    0.01523 =
         0.01745    0.00022    0.00218   -0.00049
C2    1    0.260546    0.144688    0.345098    11.00000    0.01623    0.01670 =
         0.01616    0.00097    0.00415    0.00099
C3    1    0.175900    0.066556    0.265089    11.00000    0.01607    0.02095 =
         0.01794   -0.00238    0.00344    0.00012
C4    1    0.317734    0.040591    0.143290    11.00000    0.01811    0.01714 =
         0.01549    0.00045    0.00071    0.00225
N1    3   -0.057981    0.166676    0.503860    11.00000    0.01770    0.02420 =
         0.01647   -0.00069    0.00457    0.00227
N2    3    0.289185    0.238836    0.576366    11.00000    0.02691    0.02385 =
         0.02509   -0.00583    0.00881   -0.00664
N3    3    0.268371    0.095704    0.628074    11.00000    0.01922    0.02390 =
         0.01747    0.00331   -0.00024   -0.00226
O1    4   -0.163258    0.109045    0.448169    11.00000    0.01689    0.03382 =
         0.02836   -0.00754    0.00418   -0.00454
O2    4   -0.129684    0.227140    0.557664    11.00000    0.03163    0.03148 =
         0.03230   -0.00659    0.01240    0.01077
O3    4    0.304227    0.293034    0.485016    11.00000    0.05868    0.01745 =
         0.03892   -0.00316    0.01853   -0.00767
O4    4    0.345072    0.239676    0.719044    11.00000    0.06018    0.04608 =
         0.02385   -0.01152   -0.00002   -0.02443
O5    4    0.150101    0.079715    0.726028    11.00000    0.03129    0.03675 =
         0.02199    0.00763    0.00741   -0.00608
O6    4    0.447135    0.067612    0.616924    11.00000    0.02518    0.05592 =
         0.03694    0.01932    0.00424    0.01660
O7    4    0.477669    0.078412    0.115430    11.00000    0.02525    0.02043 =
         0.02388   -0.00313    0.01148   -0.00315
O8    4    0.249848   -0.027020    0.074887    11.00000    0.02116    0.02314 =
         0.02396   -0.00817    0.00785   -0.00283
H1    2    0.417984    0.144552    0.366881    11.00000    0.01911
H2    2    0.215330    0.189411    0.282744    11.00000    0.01668
H3    2    0.178880    0.022697    0.343809    11.00000    0.02323
H4    2    0.025927    0.070794    0.212330    11.00000    0.02601
H5    2    0.340596   -0.041948    0.012269    11.00000    0.04979
HKLF    4
 
REM  ix435 in P2(1)/n
REM R1 =  0.0306 for   1484 Fo > 4sig(Fo)  and  0.0384 for all   1750 data
REM    156 parameters refined using      0 restraints
 
END
 
WGHT      0.0314      0.2537
REM Highest difference peak  0.265,  deepest hole -0.233,  1-sigma level  0.043
Q1    1   0.0782  0.1635  0.5035  11.00000  0.05    0.27
Q2    1   0.2176  0.1019  0.3179  11.00000  0.05    0.22
Q3    1   0.2394  0.0586  0.2025  11.00000  0.05    0.20
Q4    1   0.2241  0.1470  0.4326  11.00000  0.05    0.20
Q5    1   0.2336  0.1954  0.5400  11.00000  0.05    0.20
Q6    1   0.2200  0.1345  0.5688  11.00000  0.05    0.18
Q7    1   0.4831  0.0805  0.5202  11.00000  0.05    0.14
Q8    1   0.0670  0.2995  0.5008  11.00000  0.05    0.13
Q9    1   0.4749  0.0398  0.3966  11.00000  0.05    0.13
Q10   1  -0.0657  0.0118  0.3918  11.00000  0.05    0.13
Q11   1  -0.3475  0.1183  0.4660  11.00000  0.05    0.13
Q12   1   0.4459  0.0146  0.6761  11.00000  0.05    0.12
Q13   1   0.4935  0.0756  0.0071  11.00000  0.05    0.12
Q14   1  -0.0679  0.0664  0.4237  11.00000  0.05    0.12
Q15   1   0.1813  0.2937  0.4196  11.00000  0.05    0.12
Q16   1   0.5371  0.0961  0.5454  11.00000  0.05    0.11
Q17   1   0.4255  0.3423  0.5085  11.00000  0.05    0.11
Q18   1   0.2506  0.3501  0.5388  11.00000  0.05    0.11
Q19   1   0.0513  0.1165  0.7373  11.00000  0.05    0.11
Q20   1   0.3997  0.2020  0.7317  11.00000  0.05    0.11
;
