#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:16:56 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140153 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/10/4031083.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_4031083
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         'C3 H3 F N4 O8'
_chemical_formula_sum            'C3 H3 F N4 O8'
_chemical_formula_weight         242.076
_chemical_name_common            '2-fluoro-2,2-dinitroethyl nitrocarbamate'
_chemical_name_systematic        '2-fluoro-2,2-dinitroethyl nitrocarbamate'
_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
;
'Wed Mar 19 22:34:53 2014'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.728(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.716(3)
_cell_length_b                   5.9850(9)
_cell_length_c                   9.6928(12)
_cell_measurement_reflns_used    1725
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.3650
_cell_measurement_theta_min      4.6350
_cell_volume                     829.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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      173(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    3.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000  120.0000 86

  2 omega   27.00   66.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000   90.0000 39

  3 omega   17.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -90.0000 58

  4 omega   30.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000 -180.0000 57

  5 omega   34.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000   30.0000 41

  6 omega   35.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000   90.0000 63

  7 omega  -82.00   10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994   19.0000  -60.0000 92

  8 omega -109.00  -70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   60.0000 39

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      -0.0018600000
_diffrn_orient_matrix_UB_12      -0.1091949000
_diffrn_orient_matrix_UB_13      0.0278242000
_diffrn_orient_matrix_UB_21      0.0495670000
_diffrn_orient_matrix_UB_22      -0.0031244000
_diffrn_orient_matrix_UB_23      0.0205707000
_diffrn_orient_matrix_UB_31      -0.0011382000
_diffrn_orient_matrix_UB_32      0.0460423000
_diffrn_orient_matrix_UB_33      0.0669173000
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6350
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.28
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.9389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0419
_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)+(0.0292P)²+0.2126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                1364
_reflns_number_total             1690
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo5b00655_si_002.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_database_code               4031083
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
C1 C 0.15341(10) 0.4499(2) 0.23067(15) 0.0227(3) Uani 1 1 d
C2 C 0.22567(12) 0.3861(3) 0.36156(16) 0.0282(4) Uani 1 1 d
C3 C 0.38369(11) 0.2902(2) 0.40814(15) 0.0231(3) Uani 1 1 d
N1 N 0.06493(9) 0.5394(2) 0.26714(14) 0.0287(3) Uani 1 1 d
N2 N 0.18795(9) 0.6418(2) 0.15161(13) 0.0266(3) Uani 1 1 d
N3 N 0.45285(9) 0.2459(2) 0.33807(14) 0.0283(3) Uani 1 1 d
N4 N 0.54563(9) 0.2159(2) 0.40436(13) 0.0264(3) Uani 1 1 d
O1 O 0.06613(8) 0.5563(2) 0.39195(12) 0.0414(3) Uani 1 1 d
O2 O 0.00075(9) 0.5836(2) 0.16688(13) 0.0466(4) Uani 1 1 d
O3 O 0.20128(10) 0.8166(2) 0.21620(13) 0.0427(3) Uani 1 1 d
O4 O 0.20027(8) 0.6027(2) 0.03520(11) 0.0359(3) Uani 1 1 d
O5 O 0.30492(7) 0.32239(18) 0.30806(10) 0.0265(3) Uani 1 1 d
O6 O 0.39053(8) 0.3004(2) 0.53309(10) 0.0318(3) Uani 1 1 d
O7 O 0.56898(8) 0.2139(2) 0.53260(11) 0.0348(3) Uani 1 1 d
O8 O 0.59641(9) 0.1940(3) 0.32363(12) 0.0459(4) Uani 1 1 d
F1 F 0.12849(6) 0.28420(15) 0.13909(9) 0.0305(2) Uani 1 1 d
H1 H 0.2008(13) 0.259(3) 0.4016(18) 0.035(5) Uiso 1 1 d
H2 H 0.2404(12) 0.506(3) 0.4238(17) 0.028(4) Uiso 1 1 d
H3 H 0.4409(13) 0.244(3) 0.253(2) 0.035(5) 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'
F F 0.0171 0.0103 '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
F1 C1 C2 113.89(13)
F1 C1 N1 107.63(12)
C2 C1 N1 111.50(12)
F1 C1 N2 107.36(11)
C2 C1 N2 111.18(13)
N1 C1 N2 104.77(11)
O5 C2 C1 103.64(11)
O5 C2 H1 110.7(11)
C1 C2 H1 106.3(11)
O5 C2 H2 110.8(10)
C1 C2 H2 111.3(10)
H1 C2 H2 113.5(14)
O6 C3 O5 125.37(14)
O6 C3 N3 128.07(15)
O5 C3 N3 106.55(12)
O1 N1 O2 127.37(14)
O1 N1 C1 116.76(13)
O2 N1 C1 115.87(12)
O4 N2 O3 127.52(13)
O4 N2 C1 117.56(12)
O3 N2 C1 114.91(12)
N4 N3 C3 124.23(13)
N4 N3 H3 115.5(14)
C3 N3 H3 120.1(14)
O7 N4 O8 126.53(14)
O7 N4 N3 119.35(13)
O8 N4 N3 114.12(12)
C3 O5 C2 114.51(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 F1 1.3232(17)
C1 C2 1.499(2)
C1 N1 1.5253(19)
C1 N2 1.5331(19)
C2 O5 1.4358(18)
C2 H1 0.965(19)
C2 H2 0.928(18)
C3 O6 1.1928(17)
C3 O5 1.3373(18)
C3 N3 1.377(2)
N1 O1 1.2099(16)
N1 O2 1.2127(17)
N2 O4 1.2075(16)
N2 O3 1.2110(17)
N3 N4 1.3758(19)
N3 H3 0.799(19)
N4 O7 1.2085(15)
N4 O8 1.2106(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
F1 C1 C2 O5 62.00(17)
N1 C1 C2 O5 -175.95(12)
N2 C1 C2 O5 -59.43(16)
F1 C1 N1 O1 128.75(14)
C2 C1 N1 O1 3.2(2)
N2 C1 N1 O1 -117.20(14)
F1 C1 N1 O2 -50.50(18)
C2 C1 N1 O2 -176.09(14)
N2 C1 N1 O2 63.54(17)
F1 C1 N2 O4 -10.84(17)
C2 C1 N2 O4 114.34(15)
N1 C1 N2 O4 -125.08(13)
F1 C1 N2 O3 170.40(13)
C2 C1 N2 O3 -64.42(17)
N1 C1 N2 O3 56.16(16)
O6 C3 N3 N4 -3.4(3)
O5 C3 N3 N4 176.12(13)
C3 N3 N4 O7 4.8(2)
C3 N3 N4 O8 -175.16(15)
O6 C3 O5 C2 3.6(2)
N3 C3 O5 C2 -175.97(13)
C1 C2 O5 C3 170.39(13)
loop_
_iucr_refine_instructions_details
;
TITL P21c in P2(1)/c
CELL  0.71073  14.7161   5.9850   9.6928   90.000  103.728   90.000
ZERR     4.00   0.0026   0.0009   0.0012    0.000    0.014    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O    F
UNIT  12   12   16   32   4
MERG   2
OMIT    -3   1   2
SHEL   0.8 1000
FMAP   2
PLAN   20
ACTA
HTAB    2.00000
BOND   $H
CONF
L.S.  10
TEMP  -100.00
WGHT    0.029200    0.212600
FVAR       0.82652
C1    1    0.153412    0.449870    0.230665    11.00000    0.02545    0.02087 =
         0.02280   -0.00101    0.00785    0.00050
C2    1    0.225667    0.386077    0.361562    11.00000    0.02907    0.03470 =
         0.02250    0.00275    0.00972    0.00596
C3    1    0.383691    0.290159    0.408142    11.00000    0.02860    0.02117 =
         0.01799    0.00146    0.00266    0.00271
N1    3    0.064927    0.539440    0.267140    11.00000    0.02588    0.02889 =
         0.03239   -0.00110    0.00923    0.00110
N2    3    0.187949    0.641838    0.151613    11.00000    0.02665    0.02698 =
         0.02531    0.00368    0.00419    0.00231
N3    3    0.452852    0.245948    0.338066    11.00000    0.02621    0.04289 =
         0.01364    0.00009    0.00071    0.00811
N4    3    0.545630    0.215933    0.404361    11.00000    0.02954    0.02852 =
         0.01923    0.00023    0.00226    0.00460
O1    4    0.066129    0.556271    0.391947    11.00000    0.03808    0.05702 =
         0.03345   -0.00649    0.01693    0.00380
O2    4    0.000749    0.583617    0.166884    11.00000    0.03288    0.06474 =
         0.03911    0.00095    0.00230    0.01769
O3    4    0.201278    0.816632    0.216202    11.00000    0.05692    0.02592 =
         0.04690   -0.00393    0.01556   -0.00561
O4    4    0.200274    0.602663    0.035204    11.00000    0.03972    0.04572 =
         0.02333    0.00700    0.00975    0.00107
O5    4    0.304922    0.322394    0.308061    11.00000    0.02528    0.03771 =
         0.01626    0.00207    0.00429    0.00803
O6    4    0.390531    0.300418    0.533088    11.00000    0.03699    0.04295 =
         0.01512    0.00221    0.00563    0.00668
O7    4    0.568982    0.213866    0.532601    11.00000    0.03525    0.04851 =
         0.01686    0.00121   -0.00132    0.00541
O8    4    0.596412    0.193991    0.323633    11.00000    0.03149    0.08176 =
         0.02562   -0.00064    0.00930    0.01203
F1    5    0.128487    0.284201    0.139093    11.00000    0.03296    0.02745 =
         0.03165   -0.00683    0.00870   -0.00278
H1    2    0.200810    0.258841    0.401607    11.00000    0.03544
H2    2    0.240370    0.505660    0.423844    11.00000    0.02834
H3    2    0.440859    0.243898    0.253214    11.00000    0.03484
HKLF    4
 
REM  P21c in P2(1)/c
REM R1 =  0.0306 for   1364 Fo > 4sig(Fo)  and  0.0419 for all   1690 data
REM    157 parameters refined using      0 restraints
 
END
 
WGHT      0.0292      0.2126
REM Highest difference peak  0.228,  deepest hole -0.198,  1-sigma level  0.042
Q1    1   0.1867  0.4251  0.2938  11.00000  0.05    0.23
Q2    1   0.1649  0.5318  0.1890  11.00000  0.05    0.22
Q3    1   0.1182  0.4882  0.2544  11.00000  0.05    0.20
Q4    1   0.0583  0.6821  0.3417  11.00000  0.05    0.18
Q5    1   0.1435  0.3927  0.1907  11.00000  0.05    0.17
Q6    1   0.3413  0.3135  0.3560  11.00000  0.05    0.15
Q7    1   0.2661  0.3236  0.3366  11.00000  0.05    0.15
Q8    1  -0.0763  0.5843  0.2230  11.00000  0.05    0.14
Q9    1   0.6962  0.1862  0.5554  11.00000  0.05    0.13
Q10   1   0.3446  0.4083  0.5476  11.00000  0.05    0.13
Q11   1   0.2376  0.4672  0.0634  11.00000  0.05    0.13
Q12   1   0.1074  0.6891  0.0221  11.00000  0.05    0.13
Q13   1   0.3046  0.3424  0.5390  11.00000  0.05    0.12
Q14   1   0.0441  0.4120  0.3541  11.00000  0.05    0.12
Q15   1   0.3008  0.6339  0.2029  11.00000  0.05    0.12
Q16   1   0.1483  0.1732  0.2194  11.00000  0.05    0.12
Q17   1   0.5424  0.3309  0.5493  11.00000  0.05    0.12
Q18   1   0.4151  0.4586  0.5800  11.00000  0.05    0.12
Q19   1   0.4383  0.3616  0.5035  11.00000  0.05    0.12
Q20   1  -0.0474  0.4194  0.0464  11.00000  0.05    0.12
;
