#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:16:56 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140153 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/10/4031081.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_4031081
loop_
_publ_author_name
'Axthammer, Quirin J.'
'Krumm, Burkhard'
'Klapötke, Thomas M'
_publ_section_title
;
 Synthesis of Energetic Nitrocarbamates from Polynitro Alcohols and Their
 Potential as High Energetic Oxidizers.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6329
_journal_page_last               6335
_journal_paper_doi               10.1021/acs.joc.5b00655
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C4 H7 N3 O6'
_chemical_formula_sum            'C4 H7 N3 O6'
_chemical_formula_weight         193.115
_chemical_name_common            '2,2-dinitropropyl carbamate'
_chemical_name_systematic        '2,2-dinitropropyl carbamate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Fri Nov 01 18:54:21 2013'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.543(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.471(3)
_cell_length_b                   6.3990(7)
_cell_length_c                   9.7370(13)
_cell_measurement_reflns_used    807
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7180
_cell_measurement_theta_min      4.5500
_cell_volume                     804.6(2)
_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
;
_computing_publication_material
'PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).'
_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
;
  1 omega  -20.00   11.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -99.0000  -30.0000 31

  2 omega  -18.00   25.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2931  -99.0000   90.0000 43

  3 omega   35.00   69.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3869  179.0000  120.0000 34

  4 omega  -19.00   97.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3869   19.0000 -180.0000 116

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      -0.0544531000
_diffrn_orient_matrix_UB_12      0.0140966000
_diffrn_orient_matrix_UB_13      -0.0217024000
_diffrn_orient_matrix_UB_21      0.0068324000
_diffrn_orient_matrix_UB_22      0.1082150000
_diffrn_orient_matrix_UB_23      -0.0101210000
_diffrn_orient_matrix_UB_31      -0.0010942000
_diffrn_orient_matrix_UB_32      -0.0191004000
_diffrn_orient_matrix_UB_33      -0.0722269000
_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  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2921
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.20
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63255
_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    1.5942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0507
_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)+(0.0652P)²+0.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                1241
_reflns_number_total             1636
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo5b00655_si_002.cif
_cod_data_source_block           2d
_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_database_code               4031081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags
C1 C 0.1553(2) -0.2357(4) 0.6732(3) 0.0384(6) Uani 1 1 d .
H1 H 0.2129(10) -0.3136(17) 0.6528(18) 0.058 Uiso 1 1 calc R
H2 H 0.0980(14) -0.2207(4) 0.5840(18) 0.058 Uiso 1 1 calc R
H3 H 0.1304(13) -0.3129(18) 0.7451(15) 0.058 Uiso 1 1 calc R
C2 C 0.19266(18) -0.0223(4) 0.7309(2) 0.0253(5) Uani 1 1 d .
C3 C 0.2851(2) -0.0236(5) 0.8630(2) 0.0306(6) Uani 1 1 d .
C4 C 0.43175(18) -0.2421(3) 0.9011(2) 0.0228(5) Uani 1 1 d .
N1 N 0.10363(16) 0.0923(3) 0.7643(2) 0.0307(5) Uani 1 1 d .
N2 N 0.22144(16) 0.1107(3) 0.61768(19) 0.0311(5) Uani 1 1 d .
N3 N 0.49611(17) -0.3279(3) 0.8365(2) 0.0293(5) Uani 1 1 d .
O1 O 0.09575(13) 0.0729(3) 0.88455(16) 0.0347(5) Uani 1 1 d .
O2 O 0.04536(18) 0.1895(4) 0.6681(2) 0.0681(8) Uani 1 1 d .
O3 O 0.25557(16) 0.2849(3) 0.6578(2) 0.0442(5) Uani 1 1 d .
O4 O 0.21407(17) 0.0366(3) 0.50149(17) 0.0467(6) Uani 1 1 d .
O5 O 0.36804(12) -0.1028(3) 0.81393(14) 0.0289(4) Uani 1 1 d .
O6 O 0.42847(13) -0.2757(3) 1.02316(14) 0.0304(4) Uani 1 1 d .
H4 H 0.304(2) 0.113(5) 0.898(3) 0.050(8) Uiso 1 1 d .
H5 H 0.2722(18) -0.113(4) 0.931(3) 0.030(6) Uiso 1 1 d .
H6 H 0.4853(18) -0.310(4) 0.753(3) 0.019(6) Uiso 1 1 d .
H7 H 0.535(2) -0.432(4) 0.886(3) 0.033(7) 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 H1 109.5
C2 C1 H2 109.5
H1 C1 H2 109.5
C2 C1 H3 109.5
H1 C1 H3 109.5
H2 C1 H3 109.5
C1 C2 C3 114.7(2)
C1 C2 N1 108.48(19)
C3 C2 N1 109.21(17)
C1 C2 N2 111.28(18)
C3 C2 N2 107.4(2)
N1 C2 N2 105.29(17)
O5 C3 C2 104.48(17)
O5 C3 H4 107.3(18)
C2 C3 H4 111.8(17)
O5 C3 H5 110.0(15)
C2 C3 H5 109.4(15)
H4 C3 H5 113(2)
O6 C4 N3 126.8(2)
O6 C4 O5 122.2(2)
N3 C4 O5 110.99(18)
O2 N1 O1 125.8(2)
O2 N1 C2 117.43(18)
O1 N1 C2 116.70(18)
O4 N2 O3 125.5(2)
O4 N2 C2 119.2(2)
O3 N2 C2 115.21(18)
C4 N3 H6 118.3(17)
C4 N3 H7 114.6(15)
H6 N3 H7 124(2)
C4 O5 C3 116.13(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.507(3)
C1 H1 0.9889
C1 H2 0.9889
C1 H3 0.9889
C2 C3 1.515(3)
C2 N1 1.518(3)
C2 N2 1.527(3)
C3 O5 1.427(3)
C3 H4 0.95(3)
C3 H5 0.93(3)
C4 O6 1.221(2)
C4 N3 1.326(3)
C4 O5 1.356(3)
N1 O2 1.209(3)
N1 O1 1.212(2)
N2 O4 1.204(2)
N2 O3 1.226(3)
N3 H6 0.79(2)
N3 H7 0.90(3)
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
C1 C2 C3 O5 67.2(3)
N1 C2 C3 O5 -170.77(18)
N2 C2 C3 O5 -57.1(2)
C1 C2 N1 O2 -87.1(3)
C3 C2 N1 O2 147.2(3)
N2 C2 N1 O2 32.1(3)
C1 C2 N1 O1 90.8(2)
C3 C2 N1 O1 -34.9(3)
N2 C2 N1 O1 -149.97(19)
C1 C2 N2 O4 -1.3(3)
C3 C2 N2 O4 125.0(2)
N1 C2 N2 O4 -118.7(2)
C1 C2 N2 O3 -177.9(2)
C3 C2 N2 O3 -51.6(3)
N1 C2 N2 O3 64.7(2)
O6 C4 O5 C3 -10.4(3)
N3 C4 O5 C3 170.9(2)
C2 C3 O5 C4 -138.0(2)
loop_
_iucr_refine_instructions_details
;
TITL P21c in P2(1)/c
CELL  0.71073  13.4710   6.3990   9.7370   90.000  106.543   90.000
ZERR     4.00   0.0033   0.0007   0.0013    0.000    0.018    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  16   28   12   24
MERG   2
SHEL   0.8 1000
FMAP   2
PLAN   20
ACTA
BOND   $H
CONF
L.S.  10
TEMP  -173.00
WGHT    0.065200    0.154100
FVAR       0.51612
C1    1    0.155277   -0.235731    0.673242    11.00000    0.04651    0.02746 =
         0.04674   -0.00301    0.02239   -0.00357
AFIX 138
H1    2    0.212879   -0.313636    0.652837    11.00000   -1.50000
H2    2    0.097981   -0.220698    0.584017    11.00000   -1.50000
H3    2    0.130444   -0.312854    0.745073    11.00000   -1.50000
AFIX   0
C2    1    0.192663   -0.022330    0.730858    11.00000    0.02940    0.02643 =
         0.02353    0.00386    0.01322    0.00680
C3    1    0.285116   -0.023562    0.863001    11.00000    0.03433    0.03752 =
         0.02366    0.00391    0.01415    0.01325
C4    1    0.431755   -0.242123    0.901093    11.00000    0.03061    0.01897 =
         0.01818    0.00075    0.00581    0.00284
N1    3    0.103626    0.092340    0.764308    11.00000    0.03347    0.03078 =
         0.02922    0.00385    0.01110    0.00826
N2    3    0.221444    0.110686    0.617679    11.00000    0.03970    0.02849 =
         0.02774    0.00930    0.01395    0.01243
N3    3    0.496110   -0.327889    0.836514    11.00000    0.04193    0.02884 =
         0.01919    0.00684    0.01206    0.01336
O1    4    0.095751    0.072867    0.884552    11.00000    0.03577    0.04057 =
         0.03134   -0.00282    0.01524    0.00268
O2    4    0.045355    0.189453    0.668120    11.00000    0.06166    0.09941 =
         0.04912    0.03343    0.02523    0.05072
O3    4    0.255572    0.284874    0.657787    11.00000    0.05578    0.02420 =
         0.05357    0.01063    0.01704    0.00102
O4    4    0.214066    0.036595    0.501488    11.00000    0.07664    0.04013 =
         0.02801    0.00654    0.02265    0.01669
O5    4    0.368043   -0.102756    0.813928    11.00000    0.03220    0.03576 =
         0.02236    0.00936    0.01346    0.01426
O6    4    0.428467   -0.275727    1.023158    11.00000    0.04439    0.03024 =
         0.01799    0.00385    0.01101    0.01210
H4    2    0.303763    0.113091    0.898186    11.00000    0.04968
H5    2    0.272177   -0.113498    0.931061    11.00000    0.02976
H6    2    0.485302   -0.310278    0.753128    11.00000    0.01862
H7    2    0.535315   -0.432319    0.885879    11.00000    0.03316
HKLF    4
 
REM  P21c in P2(1)/c
REM R1 =  0.0507 for   1241 Fo > 4sig(Fo)  and  0.0712 for all   1636 data
REM    136 parameters refined using      0 restraints
 
END
 
WGHT      0.0652      0.1541
REM Highest difference peak  0.272,  deepest hole -0.219,  1-sigma level  0.054
Q1    1   0.2576  0.2467  0.7676  11.00000  0.05    0.27
Q2    1   0.2368 -0.0654  0.7952  11.00000  0.05    0.26
Q3    1   0.1369  0.0147  0.5006  11.00000  0.05    0.26
Q4    1   0.4431 -0.2478  0.9979  11.00000  0.05    0.25
Q5    1   0.1147 -0.0477  0.4960  11.00000  0.05    0.23
Q6    1   0.3087 -0.2113  0.7573  11.00000  0.05    0.23
Q7    1   0.3772 -0.3410  0.9754  11.00000  0.05    0.22
Q8    1   0.3725 -0.1193  0.7237  11.00000  0.05    0.20
Q9    1   0.2351  0.0477  0.7995  11.00000  0.05    0.20
Q10   1   0.2057  0.0364  0.6847  11.00000  0.05    0.19
Q11   1   0.1638  0.2101  0.9554  11.00000  0.05    0.18
Q12   1   0.5161 -0.2410  0.8826  11.00000  0.05    0.17
Q13   1   0.1730  0.0368  0.7697  11.00000  0.05    0.16
Q14   1   0.1388 -0.2056  0.5561  11.00000  0.05    0.16
Q15   1   0.2767  0.0287  0.9163  11.00000  0.05    0.15
Q16   1   0.3497 -0.2137  0.9384  11.00000  0.05    0.14
Q17   1   0.3597  0.2785  0.8231  11.00000  0.05    0.14
Q18   1   0.2959  0.1697  0.5621  11.00000  0.05    0.14
Q19   1   0.0449 -0.0389  0.4555  11.00000  0.05    0.14
Q20   1   0.4446 -0.4179  0.7362  11.00000  0.05    0.14
;
