#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:16:56 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140153 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/10/4031082.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_4031082
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         'C5 H8 N4 O8'
_chemical_formula_sum            'C5 H8 N4 O8'
_chemical_formula_weight         252.15
_chemical_name_common            '4,4,4-trinitrobutyl carbamate'
_chemical_name_systematic        '4,4,4-trinitrobutyl 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 Apr 04 05:57:03 2014'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.778(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4255(8)
_cell_length_b                   10.2488(6)
_cell_length_c                   7.4690(5)
_cell_measurement_reflns_used    1919
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.2600
_cell_measurement_theta_min      4.8180
_cell_volume                     1022.48(11)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega -109.00  -61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000  -60.0000 48

  2 omega  -76.00    2.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  -77.0000  -60.0000 78

  3 omega -104.00   30.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994    0.0000  -60.0000 134

  4 omega   25.00   93.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932 -130.0000 -137.0000 68

  5 omega   34.00  102.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   77.0000   90.0000 68

  6 omega   60.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  179.0000  -30.0000 31

  7 omega   42.00   67.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932 -179.0000 -120.0000 25

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0104315000
_diffrn_orient_matrix_UB_12      -0.0038941000
_diffrn_orient_matrix_UB_13      0.0948855000
_diffrn_orient_matrix_UB_21      0.0520301000
_diffrn_orient_matrix_UB_22      -0.0018893000
_diffrn_orient_matrix_UB_23      -0.0093694000
_diffrn_orient_matrix_UB_31      0.0019817000
_diffrn_orient_matrix_UB_32      0.0690509000
_diffrn_orient_matrix_UB_33      0.0051189000
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7159
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         4.37
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89010
_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    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0573
_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)+(0.0840P)²+0.8635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1684
_reflns_number_gt                1487
_reflns_number_total             1895
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo5b00655_si_002.cif
_cod_data_source_block           2e
_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_database_code               4031082
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 0.33815(19) 0.4780(3) 0.2383(4) 0.0339(6) Uani 1 1 d
C2 C 0.2892(2) 0.5162(3) 0.4041(4) 0.0329(6) Uani 1 1 d
C3 C 0.1851(2) 0.5743(3) 0.3631(4) 0.0354(6) Uani 1 1 d
C4 C 0.1385(2) 0.6076(3) 0.5339(4) 0.0350(6) Uani 1 1 d
C5 C 0.07182(18) 0.4987(2) 0.7722(3) 0.0300(6) Uani 1 1 d
N1 N 0.32482(19) 0.5854(3) 0.0949(4) 0.0543(8) Uani 1 1 d
N2 N 0.44935(18) 0.4544(3) 0.2790(4) 0.0496(7) Uani 1 1 d
N3 N 0.2966(2) 0.3538(3) 0.1496(4) 0.0603(8) Uani 1 1 d
N4 N 0.05607(19) 0.3836(2) 0.8459(3) 0.0375(6) Uani 1 1 d
O1 O 0.2841(2) 0.5536(5) -0.0504(4) 0.1068(14) Uani 1 1 d
O2 O 0.3531(2) 0.6913(3) 0.1445(4) 0.0762(8) Uani 1 1 d
O3 O 0.47153(18) 0.3802(3) 0.4061(4) 0.0738(8) Uani 1 1 d
O4 O 0.50675(18) 0.5138(3) 0.1949(4) 0.0792(9) Uani 1 1 d
O5 O 0.3499(3) 0.3010(5) 0.0547(7) 0.169(3) Uani 1 1 d
O6 O 0.21806(18) 0.3150(2) 0.1830(3) 0.0593(7) Uani 1 1 d
O7 O 0.11717(13) 0.48621(16) 0.6199(2) 0.0315(5) Uani 1 1 d
O8 O 0.04725(16) 0.60372(18) 0.8292(3) 0.0457(6) Uani 1 1 d
H1 H 0.288(2) 0.444(3) 0.478(4) 0.034(7) Uiso 1 1 d
H2 H 0.332(2) 0.573(3) 0.458(4) 0.041(8) Uiso 1 1 d
H3 H 0.142(3) 0.514(3) 0.287(5) 0.049(9) Uiso 1 1 d
H4 H 0.191(2) 0.657(4) 0.303(5) 0.053(9) Uiso 1 1 d
H5 H 0.187(2) 0.655(3) 0.617(4) 0.040(8) Uiso 1 1 d
H6 H 0.077(2) 0.658(3) 0.502(4) 0.037(7) Uiso 1 1 d
H7 H 0.023(2) 0.383(3) 0.933(4) 0.030(7) Uiso 1 1 d
H8 H 0.072(2) 0.316(4) 0.796(5) 0.046(9) 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 N2 112.3(2)
C2 C1 N3 113.8(2)
N2 C1 N3 105.4(2)
C2 C1 N1 110.9(2)
N2 C1 N1 107.4(2)
N3 C1 N1 106.6(2)
C1 C2 C3 113.8(2)
C1 C2 H1 108.6(17)
C3 C2 H1 111.4(17)
C1 C2 H2 103(2)
C3 C2 H2 112(2)
H1 C2 H2 108(3)
C4 C3 C2 111.6(2)
C4 C3 H3 111(2)
C2 C3 H3 110.2(19)
C4 C3 H4 105(2)
C2 C3 H4 108.7(19)
H3 C3 H4 111(3)
O7 C4 C3 107.3(2)
O7 C4 H5 107.0(17)
C3 C4 H5 109.9(17)
O7 C4 H6 111.0(17)
C3 C4 H6 109.0(17)
H5 C4 H6 112(2)
O8 C5 N4 125.6(2)
O8 C5 O7 122.7(2)
N4 C5 O7 111.7(2)
O2 N1 O1 128.5(4)
O2 N1 C1 115.0(3)
O1 N1 C1 116.4(3)
O4 N2 O3 126.6(3)
O4 N2 C1 118.9(3)
O3 N2 C1 114.3(2)
O6 N3 O5 125.4(3)
O6 N3 C1 119.3(2)
O5 N3 C1 115.2(3)
C5 N4 H7 117(2)
C5 N4 H8 120(2)
H7 N4 H8 122(3)
C5 O7 C4 114.89(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.511(4)
C1 N2 1.513(3)
C1 N3 1.515(4)
C1 N1 1.533(4)
C2 C3 1.522(4)
C2 H1 0.92(3)
C2 H2 0.89(3)
C3 C4 1.514(4)
C3 H3 0.98(4)
C3 H4 0.97(4)
C4 O7 1.442(3)
C4 H5 0.99(3)
C4 H6 0.98(3)
C5 O8 1.216(3)
C5 N4 1.327(3)
C5 O7 1.349(3)
N1 O2 1.196(4)
N1 O1 1.209(4)
N2 O4 1.207(4)
N2 O3 1.229(4)
N3 O6 1.177(3)
N3 O5 1.187(4)
N4 H7 0.82(3)
N4 H8 0.82(4)
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 165.0(2)
N3 C1 C2 C3 -75.3(3)
N1 C1 C2 C3 44.9(3)
C1 C2 C3 C4 178.6(2)
C2 C3 C4 O7 -69.1(3)
C2 C1 N1 O2 54.7(3)
N2 C1 N1 O2 -68.3(3)
N3 C1 N1 O2 179.1(2)
C2 C1 N1 O1 -122.7(3)
N2 C1 N1 O1 114.3(3)
N3 C1 N1 O1 1.8(3)
C2 C1 N2 O4 -125.1(3)
N3 C1 N2 O4 110.4(3)
N1 C1 N2 O4 -2.9(4)
C2 C1 N2 O3 50.4(4)
N3 C1 N2 O3 -74.1(3)
N1 C1 N2 O3 172.5(3)
C2 C1 N3 O6 18.3(4)
N2 C1 N3 O6 141.8(3)
N1 C1 N3 O6 -104.3(3)
C2 C1 N3 O5 -159.2(4)
N2 C1 N3 O5 -35.7(5)
N1 C1 N3 O5 78.2(5)
O8 C5 O7 C4 2.7(4)
N4 C5 O7 C4 -178.9(2)
C3 C4 O7 C5 -177.8(2)
loop_
_iucr_refine_instructions_details
;
TITL P21_c in P2(1)/c
CELL  0.71073  13.4255  10.2488   7.4690   90.000   95.778   90.000
ZERR     4.00   0.0008   0.0006   0.0005    0.000    0.006    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  20   32   16   32
MERG   2
OMIT     5   3   1
OMIT     1   2   0
OMIT     1   3   2
OMIT     4   3   1
OMIT    -3   0   2
OMIT     0   4   0
OMIT    -2   4   2
SHEL 0.825 1000
FMAP   2
PLAN   20
ACTA    50.00
BOND   $H
CONF
L.S.   5
TEMP  -100.00
WGHT    0.084000    0.863500
FVAR       7.41580
C1    1    0.338149    0.478018    0.238275    11.00000    0.02721    0.03904 =
         0.03636   -0.00543    0.00701   -0.00202
C2    1    0.289169    0.516164    0.404116    11.00000    0.02882    0.03987 =
         0.03114   -0.00187    0.00789   -0.00076
C3    1    0.185063    0.574275    0.363146    11.00000    0.03317    0.04030 =
         0.03443    0.00721    0.01131    0.00578
C4    1    0.138507    0.607572    0.533873    11.00000    0.03700    0.03211 =
         0.03836    0.00176    0.01573    0.00155
C5    1    0.071819    0.498653    0.772222    11.00000    0.02352    0.03644 =
         0.03092   -0.00392    0.00774   -0.00161
N1    3    0.324822    0.585375    0.094871    11.00000    0.03643    0.08385 =
         0.04566    0.00885    0.01893   -0.00350
N2    3    0.449352    0.454357    0.278972    11.00000    0.03054    0.07235 =
         0.04643   -0.00605    0.00681    0.00910
N3    3    0.296611    0.353783    0.149642    11.00000    0.04740    0.05897 =
         0.07678   -0.03594    0.01677   -0.00770
N4    3    0.056070    0.383583    0.845873    11.00000    0.04659    0.03493 =
         0.03402    0.00211    0.01918    0.00578
O1    4    0.284096    0.553641   -0.050359    11.00000    0.06194    0.21141 =
         0.04435    0.03657   -0.00759   -0.04115
O2    4    0.353097    0.691263    0.144533    11.00000    0.07921    0.05979 =
         0.09591    0.02017    0.04006   -0.00488
O3    4    0.471528    0.380248    0.406139    11.00000    0.04564    0.06973 =
         0.10717    0.01876    0.01293    0.02176
O4    4    0.506754    0.513780    0.194933    11.00000    0.03342    0.15049 =
         0.05631    0.00824    0.01796   -0.00418
O5    4    0.349886    0.301019    0.054712    11.00000    0.10667    0.17181 =
         0.24115   -0.16897    0.08589   -0.04961
O6    4    0.218060    0.314972    0.182971    11.00000    0.05935    0.04452 =
         0.07347   -0.00246    0.00369   -0.01884
O7    4    0.117167    0.486213    0.619883    11.00000    0.03554    0.03152 =
         0.02944    0.00041    0.01241    0.00388
O8    4    0.047252    0.603725    0.829205    11.00000    0.05994    0.03330 =
         0.04957   -0.00866    0.03288   -0.00625
H1    2    0.288145    0.444404    0.477933    11.00000    0.03431
H2    2    0.331612    0.573233    0.458431    11.00000    0.04125
H3    2    0.142096    0.514424    0.287015    11.00000    0.04910
H4    2    0.190971    0.657388    0.303054    11.00000    0.05251
H5    2    0.187252    0.655096    0.617401    11.00000    0.03965
H6    2    0.076989    0.657734    0.502386    11.00000    0.03664
H7    2    0.023177    0.382690    0.932707    11.00000    0.03001
H8    2    0.071806    0.316127    0.796264    11.00000    0.04607
HKLF    4
 
REM  P21_c in P2(1)/c
REM R1 =  0.0573 for   1487 Fo > 4sig(Fo)  and  0.0737 for all   1895 data
REM    186 parameters refined using      0 restraints
 
END
 
WGHT      0.0840      0.8635
REM Highest difference peak  0.535,  deepest hole -0.353,  1-sigma level  0.056
Q1    1   0.4425  0.3532  0.2929  11.00000  0.05    0.54
Q2    1   0.4643  0.3032  0.1891  11.00000  0.05    0.45
Q3    1   0.2843  0.4126 -0.0612  11.00000  0.05    0.41
Q4    1   0.3957  0.5968  0.1589  11.00000  0.05    0.35
Q5    1   0.4573  0.6225  0.1555  11.00000  0.05    0.31
Q6    1   0.3084  0.4907  0.3113  11.00000  0.05    0.22
Q7    1   0.0943  0.5630  0.8808  11.00000  0.05    0.22
Q8    1   0.3451  0.2584  0.1401  11.00000  0.05    0.22
Q9    1   0.1619  0.5789  0.4414  11.00000  0.05    0.21
Q10   1   0.3090  0.6592  0.0612  11.00000  0.05    0.21
Q11   1   0.2652  0.5873 -0.0236  11.00000  0.05    0.21
Q12   1   0.4799  0.4537  0.4187  11.00000  0.05    0.20
Q13   1   0.0950  0.4929  0.6792  11.00000  0.05    0.15
Q14   1   0.3175  0.4218  0.2194  11.00000  0.05    0.15
Q15   1   0.4944  0.3335  0.4625  11.00000  0.05    0.14
Q16   1   0.3770  0.4696  0.2547  11.00000  0.05    0.14
Q17   1   0.1438  0.5428  0.6113  11.00000  0.05    0.14
Q18   1   0.3803  0.2936  0.0443  11.00000  0.05    0.13
Q19   1   0.3031  0.4458  0.1693  11.00000  0.05    0.13
Q20   1   0.0157  0.7064  0.9394  11.00000  0.05    0.12
;
