#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:16:56 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140153 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/10/4031080.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_4031080
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         252.139
_chemical_name_common            '2,2-dinitropropane-1,3-diyl dicarbamate'
_chemical_name_systematic        '2,2-dinitropropane-1,3-diyl dicarbamate'
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Thu Jul 31 12:40:44 2014'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3762(12)
_cell_length_b                   9.3483(7)
_cell_length_c                   6.8213(6)
_cell_measurement_reflns_used    1078
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.9140
_cell_measurement_theta_min      4.5200
_cell_volume                     980.50(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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 0.991
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details
;
  1 omega -102.00  -41.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000 -150.0000 61

  2 omega  -88.00  -52.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000   30.0000 36

  3 omega  -46.00   73.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -19.0000  -30.0000 119

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0065271000
_diffrn_orient_matrix_UB_12      0.0293277000
_diffrn_orient_matrix_UB_13      0.0947754000
_diffrn_orient_matrix_UB_21      0.0451330000
_diffrn_orient_matrix_UB_22      -0.0145447000
_diffrn_orient_matrix_UB_23      -0.0073260000
_diffrn_orient_matrix_UB_31      0.0068538000
_diffrn_orient_matrix_UB_32      0.0684420000
_diffrn_orient_matrix_UB_33      -0.0422558000
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4820
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.13
_diffrn_reflns_theta_min         4.26
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.7081
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0420
_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)+(0.0281P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2185
_reflns_number_total             2763
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo5b00655_si_002.cif
_cod_data_source_block           2c
_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_database_code               4031080
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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 0.05285(12) 0.3031(2) 0.2517(3) 0.0199(4) Uani 1 1 d
C2 C 0.17026(13) 0.2639(2) 0.0346(3) 0.0229(4) Uani 1 1 d
C3 C 0.25625(12) 0.34263(18) 0.0604(3) 0.0201(4) Uani 1 1 d
C4 C 0.32807(13) 0.2599(2) -0.0408(4) 0.0237(4) Uani 1 1 d
C5 C 0.45159(12) 0.30645(19) -0.2294(3) 0.0201(4) Uani 1 1 d
N1 N -0.00385(11) 0.4006(2) 0.3111(3) 0.0277(4) Uani 1 1 d
N2 N 0.27726(11) 0.36994(16) 0.2757(3) 0.0232(3) Uani 1 1 d
N3 N 0.24943(11) 0.49129(17) -0.0311(2) 0.0234(3) Uani 1 1 d
N4 N 0.51083(12) 0.4028(2) -0.2798(3) 0.0276(4) Uani 1 1 d
O1 O 0.06295(9) 0.18388(13) 0.3193(2) 0.0257(3) Uani 1 1 d
O2 O 0.09869(8) 0.34986(13) 0.0920(2) 0.0224(3) Uani 1 1 d
O3 O 0.21860(10) 0.41432(17) 0.3788(2) 0.0378(4) Uani 1 1 d
O4 O 0.35119(10) 0.34678(17) 0.3303(3) 0.0399(4) Uani 1 1 d
O5 O 0.22126(11) 0.49409(16) -0.1966(3) 0.0408(4) Uani 1 1 d
O6 O 0.27429(9) 0.59452(14) 0.0620(2) 0.0335(4) Uani 1 1 d
O7 O 0.39808(9) 0.35537(13) -0.0849(2) 0.0240(3) Uani 1 1 d
O8 O 0.44427(9) 0.18594(14) -0.2957(2) 0.0264(3) Uani 1 1 d
H1 H -0.0299(15) 0.381(3) 0.429(4) 0.033(7) Uiso 1 1 d
H2 H 0.003(2) 0.488(3) 0.264(4) 0.056(8) Uiso 1 1 d
H3 H 0.1721(13) 0.176(2) 0.109(4) 0.021(5) Uiso 1 1 d
H4 H 0.1634(13) 0.245(2) -0.104(4) 0.021(5) Uiso 1 1 d
H5 H 0.3447(12) 0.184(2) 0.043(3) 0.016(5) Uiso 1 1 d
H6 H 0.3053(15) 0.222(2) -0.158(4) 0.034(7) Uiso 1 1 d
H7 H 0.5033(18) 0.487(3) -0.245(3) 0.035(7) Uiso 1 1 d
H8 H 0.5433(14) 0.389(2) -0.383(4) 0.028(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
O1 C1 N1 126.75(19)
O1 C1 O2 121.92(17)
N1 C1 O2 111.26(17)
O2 C2 C3 111.55(15)
O2 C2 H3 111.1(12)
C3 C2 H3 109.0(12)
O2 C2 H4 106.9(13)
C3 C2 H4 107.3(12)
H3 C2 H4 110.9(18)
C4 C3 C2 109.47(15)
C4 C3 N2 111.70(16)
C2 C3 N2 112.11(16)
C4 C3 N3 109.15(15)
C2 C3 N3 109.44(15)
N2 C3 N3 104.83(13)
O7 C4 C3 109.05(15)
O7 C4 H5 113.2(12)
C3 C4 H5 107.9(12)
O7 C4 H6 109.8(14)
C3 C4 H6 108.0(14)
H5 C4 H6 108.8(19)
O8 C5 N4 126.50(19)
O8 C5 O7 121.50(16)
N4 C5 O7 111.97(17)
C1 N1 H1 114.6(15)
C1 N1 H2 117(2)
H1 N1 H2 124(3)
O4 N2 O3 125.22(18)
O4 N2 C3 117.61(17)
O3 N2 C3 117.17(15)
O5 N3 O6 125.63(17)
O5 N3 C3 115.21(17)
O6 N3 C3 119.12(16)
C5 N4 H7 118.2(19)
C5 N4 H8 120.3(15)
H7 N4 H8 117(2)
C1 O2 C2 116.01(15)
C5 O7 C4 113.41(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.216(2)
C1 N1 1.324(2)
C1 O2 1.369(2)
C2 O2 1.418(2)
C2 C3 1.524(3)
C2 H3 0.97(2)
C2 H4 0.97(2)
C3 C4 1.515(3)
C3 N2 1.525(3)
C3 N3 1.527(2)
C4 O7 1.430(2)
C4 H5 0.95(2)
C4 H6 0.94(3)
C5 O8 1.219(2)
C5 N4 1.326(3)
C5 O7 1.363(2)
N1 H1 0.92(3)
N1 H2 0.89(3)
N2 O4 1.216(2)
N2 O3 1.217(2)
N3 O5 1.209(2)
N3 O6 1.217(2)
N4 H7 0.83(3)
N4 H8 0.87(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
O2 C2 C3 C4 -168.34(17)
O2 C2 C3 N2 67.1(2)
O2 C2 C3 N3 -48.7(2)
C2 C3 C4 O7 157.18(17)
N2 C3 C4 O7 -78.0(2)
N3 C3 C4 O7 37.4(2)
C4 C3 N2 O4 12.3(2)
C2 C3 N2 O4 135.59(17)
N3 C3 N2 O4 -105.78(17)
C4 C3 N2 O3 -168.24(16)
C2 C3 N2 O3 -45.0(2)
N3 C3 N2 O3 73.68(18)
C4 C3 N3 O5 69.9(2)
C2 C3 N3 O5 -49.8(2)
N2 C3 N3 O5 -170.26(17)
C4 C3 N3 O6 -107.9(2)
C2 C3 N3 O6 132.30(18)
N2 C3 N3 O6 11.9(2)
O1 C1 O2 C2 -12.2(3)
N1 C1 O2 C2 170.60(17)
C3 C2 O2 C1 -114.59(19)
O8 C5 O7 C4 -7.6(3)
N4 C5 O7 C4 174.06(19)
C3 C4 O7 C5 -159.30(17)
loop_
_iucr_refine_instructions_details
;
TITL Pna2 in Pna2(1)
CELL  0.71073  15.3762   9.3483   6.8213   90.000   90.000   90.000
ZERR     4.00   0.0012   0.0007   0.0006    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y,   Z
SYMM  1/2 - X, 1/2 + Y, 1/2 + Z
SFAC  C    H    N    O
UNIT  20   32   16   32
MERG   2
OMIT     3   4   0
OMIT     5   2  -2
OMIT    13   3  -5
OMIT     6   8  -7
OMIT    11   3   8
OMIT     5   2   2
OMIT    11   6   2
FMAP   2
PLAN   20
ACTA    50.00
BOND   $H
CONF
L.S.  50
TEMP  -100.00
WGHT    0.028100
FVAR       0.61916
C1    1    0.052849    0.303100    0.251666    11.00000    0.01728    0.02048 =
         0.02187    0.00042    0.00246   -0.00354
C2    1    0.170256    0.263862    0.034552    11.00000    0.01945    0.02503 =
         0.02427   -0.00402    0.00509   -0.00081
C3    1    0.256246    0.342633    0.060446    11.00000    0.02125    0.01805 =
         0.02115   -0.00051    0.00180   -0.00028
C4    1    0.328073    0.259936   -0.040773    11.00000    0.02087    0.01669 =
         0.03357   -0.00467    0.00816   -0.00262
C5    1    0.451588    0.306454   -0.229376    11.00000    0.01972    0.01965 =
         0.02087    0.00195    0.00277    0.00475
N1    3   -0.003847    0.400554    0.311053    11.00000    0.02860    0.02014 =
         0.03439    0.00265    0.01338    0.00181
N2    3    0.277262    0.369936    0.275678    11.00000    0.02690    0.02105 =
         0.02153   -0.00008   -0.00101   -0.00032
N3    3    0.249428    0.491292   -0.031110    11.00000    0.02434    0.02285 =
         0.02290    0.00129    0.00640    0.00239
N4    3    0.510835    0.402807   -0.279760    11.00000    0.02822    0.02376 =
         0.03077   -0.00340    0.01366   -0.00178
O1    4    0.062949    0.183882    0.319324    11.00000    0.02832    0.01824 =
         0.03055    0.00297    0.00601   -0.00071
O2    4    0.098692    0.349856    0.092038    11.00000    0.02054    0.02377 =
         0.02289    0.00523    0.00546    0.00180
O3    4    0.218598    0.414319    0.378801    11.00000    0.03867    0.05050 =
         0.02435   -0.01102    0.00521    0.00520
O4    4    0.351186    0.346776    0.330283    11.00000    0.02942    0.05637 =
         0.03402    0.00103   -0.01199    0.00367
O5    4    0.221264    0.494087   -0.196611    11.00000    0.05527    0.04387 =
         0.02319    0.01013   -0.00197    0.00107
O6    4    0.274291    0.594521    0.062013    11.00000    0.04121    0.01892 =
         0.04033   -0.00316    0.00698   -0.00276
O7    4    0.398083    0.355367   -0.084908    11.00000    0.02094    0.02045 =
         0.03069   -0.00669    0.01016   -0.00420
O8    4    0.444266    0.185943   -0.295673    11.00000    0.03310    0.01665 =
         0.02941   -0.00023    0.00988    0.00298
H1    2   -0.029929    0.380601    0.428535    11.00000    0.03325
H2    2    0.002622    0.488317    0.263618    11.00000    0.05574
H3    2    0.172082    0.175961    0.108706    11.00000    0.02097
H4    2    0.163417    0.244591   -0.104002    11.00000    0.02072
H5    2    0.344679    0.183572    0.042652    11.00000    0.01613
H6    2    0.305267    0.221588   -0.157896    11.00000    0.03367
H7    2    0.503296    0.486848   -0.244654    11.00000    0.03491
H8    2    0.543327    0.389431   -0.383069    11.00000    0.02838
HKLF    4
 
REM  Pna2 in Pna2(1)
REM R1 =  0.0420 for   2185 Fo > 4sig(Fo)  and  0.0616 for all   2763 data
REM    186 parameters refined using      1 restraints
 
END
 
WGHT      0.0281      0.0000
REM Highest difference peak  0.254,  deepest hole -0.213,  1-sigma level  0.047
Q1    1   0.2583  0.4093  0.0208  11.00000  0.05    0.25
Q2    1   0.2204  0.4954  0.3195  11.00000  0.05    0.20
Q3    1   0.2775  0.4174 -0.3535  11.00000  0.05    0.20
Q4    1   0.2090  0.3272  0.0153  11.00000  0.05    0.18
Q5    1   0.4627  0.1310 -0.0228  11.00000  0.05    0.18
Q6    1   0.4046  0.1264 -0.2318  11.00000  0.05    0.17
Q7    1   0.4963  0.3374 -0.2091  11.00000  0.05    0.17
Q8    1   0.2599  0.3670  0.1648  11.00000  0.05    0.17
Q9    1   0.2988  0.3154  0.0257  11.00000  0.05    0.17
Q10   1   0.0154  0.3411  0.2696  11.00000  0.05    0.16
Q11   1   0.4085  0.2273 -0.4090  11.00000  0.05    0.16
Q12   1   0.2049  0.4263  0.0279  11.00000  0.05    0.16
Q13   1   0.3512  0.4671  0.1235  11.00000  0.05    0.16
Q14   1   0.5284  0.1849 -0.3528  11.00000  0.05    0.16
Q15   1   0.2213  0.3541 -0.2933  11.00000  0.05    0.15
Q16   1   0.1016  0.4459  0.1673  11.00000  0.05    0.15
Q17   1   0.3990  0.1012 -0.0390  11.00000  0.05    0.15
Q18   1   0.1510  0.4584  0.1744  11.00000  0.05    0.15
Q19   1   0.2188  0.2996  0.5615  11.00000  0.05    0.15
Q20   1   0.3595  0.4368 -0.2348  11.00000  0.05    0.15
;
