#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/10/4031084.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_4031084
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 H6 N6 O12'
_chemical_formula_sum            'C5 H6 N6 O12'
_chemical_formula_weight         342.134
_chemical_name_common
'2,2-dinitropropane-1,3-diyl bis(nitrocarbamate)'
_chemical_name_systematic
'2,2-dinitropropane-1,3-diyl bis(nitrocarbamate)'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.1269(5)
_cell_length_b                   9.6783(4)
_cell_length_c                   26.0397(12)
_cell_measurement_temperature    100(2)
_cell_volume                     2552.2(2)
_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_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8994
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.21
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96076
_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    1.7809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0307P)²+1.1263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                2181
_reflns_number_total             2603
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo5b00655_si_002.cif
_cod_data_source_block           3c
_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_database_code               4031084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
H4 H 1.0404(18) 0.0301(17) 0.6211(6) 0.021(4) Uiso 1 1 d
H6 H 1.2690(18) 0.2815(19) 0.5286(7) 0.024(5) Uiso 1 1 d
H5 H 1.1831(18) 0.0073(17) 0.6407(6) 0.020(4) Uiso 1 1 d
H2 H 0.9477(16) 0.3046(15) 0.7055(6) 0.016(4) Uiso 1 1 d
H1 H 0.6790(18) 0.055(2) 0.6333(7) 0.027(5) Uiso 1 1 d
H3 H 0.9857(17) 0.3195(17) 0.6475(7) 0.022(4) Uiso 1 1 d
O4 O 0.85759(10) 0.16978(9) 0.66012(4) 0.0163(2) Uani 1 1 d
O3 O 0.73742(11) 0.35951(10) 0.63955(4) 0.0221(2) Uani 1 1 d
O10 O 1.21147(12) -0.02207(10) 0.54849(4) 0.0265(3) Uani 1 1 d
O9 O 1.16807(10) 0.16749(9) 0.59581(4) 0.0168(2) Uani 1 1 d
C3 C 1.08207(14) 0.15803(14) 0.68019(5) 0.0147(3) Uani 1 1 d
O8 O 1.19192(11) 0.36390(11) 0.70146(4) 0.0251(3) Uani 1 1 d
O1 O 0.46076(11) 0.06245(11) 0.61289(4) 0.0251(3) Uani 1 1 d
N4 N 1.20274(12) 0.23886(12) 0.69824(5) 0.0186(3) Uani 1 1 d
O5 O 1.00867(11) -0.05454(10) 0.71273(4) 0.0241(3) Uani 1 1 d
N2 N 0.66285(12) 0.13541(13) 0.62722(5) 0.0166(3) Uani 1 1 d
N3 N 1.05185(12) 0.05841(12) 0.72446(4) 0.0185(3) Uani 1 1 d
O7 O 1.30146(11) 0.17153(12) 0.70768(5) 0.0328(3) Uani 1 1 d
C4 C 1.11725(16) 0.07174(15) 0.63340(5) 0.0177(3) Uani 1 1 d
N6 N 1.34221(15) 0.16369(14) 0.47857(5) 0.0268(3) Uani 1 1 d
N1 N 0.53555(13) 0.16127(13) 0.61083(5) 0.0217(3) Uani 1 1 d
C1 C 0.75083(14) 0.23648(14) 0.64198(5) 0.0148(3) Uani 1 1 d
O6 O 1.07132(12) 0.10102(12) 0.76800(4) 0.0298(3) Uani 1 1 d
N5 N 1.26475(14) 0.19827(14) 0.52056(5) 0.0219(3) Uani 1 1 d
C5 C 1.21559(15) 0.10068(14) 0.55411(5) 0.0176(3) Uani 1 1 d
C2 C 0.96718(14) 0.25726(14) 0.67362(6) 0.0157(3) Uani 1 1 d
O11 O 1.35484(17) 0.04311(13) 0.46733(5) 0.0466(4) Uani 1 1 d
O12 O 1.39024(13) 0.26289(13) 0.45610(4) 0.0342(3) Uani 1 1 d
O2 O 0.50934(14) 0.27572(12) 0.59482(6) 0.0481(4) Uani 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
C1 O4 C2 115.04(10)
C5 O9 C4 111.38(10)
C2 C3 C4 115.90(12)
C2 C3 N4 108.92(11)
C4 C3 N4 109.94(12)
C2 C3 N3 109.23(11)
C4 C3 N3 107.70(11)
N4 C3 N3 104.53(10)
O8 N4 O7 126.25(13)
O8 N4 C3 117.31(12)
O7 N4 C3 116.44(11)
C1 N2 N1 124.14(12)
C1 N2 H1 119.8(13)
N1 N2 H1 115.0(14)
O5 N3 O6 126.44(12)
O5 N3 C3 116.62(11)
O6 N3 C3 116.93(11)
O9 C4 C3 105.94(11)
O9 C4 H4 110.0(10)
C3 C4 H4 108.5(10)
O9 C4 H5 108.2(10)
C3 C4 H5 111.8(10)
H4 C4 H5 112.2(14)
O11 N6 O12 126.74(14)
O11 N6 N5 118.91(13)
O12 N6 N5 114.34(12)
O2 N1 O1 126.49(14)
O2 N1 N2 118.43(13)
O1 N1 N2 115.05(12)
O3 C1 O4 125.86(13)
O3 C1 N2 128.06(14)
O4 C1 N2 106.08(11)
C5 N5 N6 122.56(13)
C5 N5 H6 121.5(12)
N6 N5 H6 113.7(13)
O10 C5 O9 124.06(13)
O10 C5 N5 127.90(14)
O9 C5 N5 108.03(12)
O4 C2 C3 104.26(11)
O4 C2 H2 109.3(10)
C3 C2 H2 111.0(10)
O4 C2 H3 111.0(11)
C3 C2 H3 109.8(11)
H2 C2 H3 111.2(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C1 1.3449(17)
O4 C2 1.4395(17)
O3 C1 1.2001(16)
O10 C5 1.1977(17)
O9 C5 1.3524(16)
O9 C4 1.4428(17)
C3 C2 1.518(2)
C3 C4 1.5196(19)
C3 N4 1.5251(18)
C3 N3 1.5335(17)
O8 N4 1.2180(16)
O1 N1 1.2211(16)
N4 O7 1.2185(16)
O5 N3 1.2164(16)
N2 C1 1.3779(19)
N2 N1 1.3809(18)
N2 H1 0.812(19)
N3 O6 1.2224(16)
C4 H4 0.934(18)
C4 H5 0.933(18)
N6 O11 1.2100(17)
N6 O12 1.2251(17)
N6 N5 1.3865(18)
N1 O2 1.2129(17)
N5 C5 1.3796(19)
N5 H6 0.833(19)
C2 H2 0.969(16)
C2 H3 0.928(18)
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
C2 C3 N4 O8 -4.09(16)
C4 C3 N4 O8 123.91(13)
N3 C3 N4 O8 -120.75(13)
C2 C3 N4 O7 176.47(12)
C4 C3 N4 O7 -55.53(16)
N3 C3 N4 O7 59.81(15)
C2 C3 N3 O5 97.97(14)
C4 C3 N3 O5 -28.69(17)
N4 C3 N3 O5 -145.59(12)
C2 C3 N3 O6 -80.81(15)
C4 C3 N3 O6 152.54(13)
N4 C3 N3 O6 35.63(16)
C5 O9 C4 C3 173.69(12)
C2 C3 C4 O9 67.62(16)
N4 C3 C4 O9 -56.42(15)
N3 C3 C4 O9 -169.74(11)
C1 N2 N1 O2 21.3(2)
C1 N2 N1 O1 -160.58(13)
C2 O4 C1 O3 -5.1(2)
C2 O4 C1 N2 174.82(11)
N1 N2 C1 O3 -6.2(2)
N1 N2 C1 O4 173.79(12)
O11 N6 N5 C5 8.8(2)
O12 N6 N5 C5 -172.05(14)
C4 O9 C5 O10 2.5(2)
C4 O9 C5 N5 -178.73(12)
N6 N5 C5 O10 -13.5(3)
N6 N5 C5 O9 167.77(13)
C1 O4 C2 C3 -166.83(11)
C4 C3 C2 O4 59.23(15)
N4 C3 C2 O4 -176.21(10)
N3 C3 C2 O4 -62.60(13)
loop_
_iucr_refine_instructions_details
;
TITL ortho in Pbca
CELL  0.71073  10.1269   9.6783  26.0397   90.000   90.000   90.000
ZERR     8.00   0.0005   0.0004   0.0012    0.000    0.000    0.000
LATT   1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  - X, 1/2 + Y, 1/2 - Z
SYMM  1/2 + X, 1/2 - Y, - Z
SFAC  C    H    N    O
UNIT  40   48   48   96
MERG   2
SHEL 0.8 1000
FMAP   2
PLAN   20
ACTA
HTAB    2.00000
BOND   $H
CONF
L.S.  10
TEMP  -173.00
WGHT    0.030700    1.126300
FVAR       0.11870
H4    2    1.040387    0.030058    0.621063    11.00000    0.02077
H6    2    1.268990    0.281488    0.528557    11.00000    0.02444
H5    2    1.183105    0.007299    0.640693    11.00000    0.02012
H2    2    0.947726    0.304631    0.705525    11.00000    0.01574
H1    2    0.678976    0.054894    0.633336    11.00000    0.02664
H3    2    0.985676    0.319516    0.647515    11.00000    0.02225
MOLE    1
O4    4    0.857592    0.169782    0.660117    11.00000    0.01580    0.01155 =
         0.02162    0.00176   -0.00376   -0.00061
O3    4    0.737415    0.359510    0.639552    11.00000    0.02047    0.01084 =
         0.03511   -0.00042   -0.00178    0.00114
O10   4    1.211469   -0.022072    0.548486    11.00000    0.03743    0.01488 =
         0.02711   -0.00529    0.00448   -0.00212
O9    4    1.168068    0.167489    0.595810    11.00000    0.02155    0.01330 =
         0.01553    0.00057    0.00462    0.00026
C3    1    1.082072    0.158028    0.680195    11.00000    0.01575    0.01368 =
         0.01480    0.00205    0.00077   -0.00316
O8    4    1.191921    0.363901    0.701463    11.00000    0.02294    0.01629 =
         0.03599   -0.00362    0.00170   -0.00420
O1    4    0.460762    0.062448    0.612894    11.00000    0.01709    0.02331 =
         0.03488   -0.00229   -0.00181   -0.00384
N4    3    1.202742    0.238862    0.698236    11.00000    0.01608    0.01987 =
         0.01979   -0.00077    0.00120   -0.00161
O5    4    1.008668   -0.054537    0.712733    11.00000    0.02482    0.01845 =
         0.02889    0.00745    0.00041   -0.00445
N2    3    0.662853    0.135410    0.627217    11.00000    0.01639    0.01045 =
         0.02282   -0.00010   -0.00398    0.00176
N3    3    1.051854    0.058414    0.724458    11.00000    0.01581    0.02000 =
         0.01982    0.00584    0.00065    0.00164
O7    4    1.301463    0.171526    0.707677    11.00000    0.01853    0.02811 =
         0.05178   -0.00196   -0.00842    0.00338
C4    1    1.117245    0.071742    0.633400    11.00000    0.02059    0.01329 =
         0.01911    0.00228    0.00346    0.00028
N6    3    1.342206    0.163689    0.478573    11.00000    0.03495    0.02814 =
         0.01721   -0.00330    0.00551    0.00030
N1    3    0.535546    0.161269    0.610831    11.00000    0.02148    0.01597 =
         0.02767   -0.00379   -0.00643    0.00347
C1    1    0.750827    0.236483    0.641985    11.00000    0.01631    0.01321 =
         0.01481   -0.00042    0.00123    0.00053
O6    4    1.071316    0.101020    0.767999    11.00000    0.03789    0.03582 =
         0.01571    0.00224    0.00024   -0.00180
N5    3    1.264750    0.198269    0.520557    11.00000    0.03245    0.01652 =
         0.01679   -0.00372    0.00655   -0.00076
C5    1    1.215589    0.100676    0.554107    11.00000    0.01916    0.01681 =
         0.01690   -0.00235   -0.00156    0.00016
C2    1    0.967176    0.257259    0.673623    11.00000    0.01548    0.01362 =
         0.01786   -0.00086   -0.00027   -0.00242
O11   4    1.354844    0.043109    0.467327    11.00000    0.07938    0.02824 =
         0.03210   -0.00821    0.02291    0.00840
O12   4    1.390237    0.262888    0.456099    11.00000    0.04297    0.03800 =
         0.02167    0.00026    0.01053   -0.00937
O2    4    0.509338    0.275715    0.594821    11.00000    0.04220    0.01602 =
         0.08610    0.00412   -0.03727    0.00404
HKLF    4
 
REM  ortho in Pbca
REM R1 =  0.0295 for   2181 Fo > 4sig(Fo)  and  0.0388 for all   2603 data
REM    232 parameters refined using      0 restraints
 
END
 
WGHT      0.0307      1.1263
REM Highest difference peak  0.302,  deepest hole -0.215,  1-sigma level  0.043
Q1    1   1.0981  0.1213  0.6596  11.00000  0.05    0.30
Q2    1   1.0308  0.2032  0.6752  11.00000  0.05    0.29
Q3    1   1.1331  0.1986  0.6870  11.00000  0.05    0.29
Q4    1   1.0754  0.1194  0.6975  11.00000  0.05    0.22
Q5    1   0.7007  0.1947  0.6264  11.00000  0.05    0.22
Q6    1   1.2915  0.1773  0.6706  11.00000  0.05    0.20
Q7    1   0.9079  0.2168  0.6684  11.00000  0.05    0.18
Q8    1   0.4999  0.2540  0.6246  11.00000  0.05    0.17
Q9    1   1.0841  0.1989  0.7601  11.00000  0.05    0.16
Q10   1   0.6089  0.1523  0.6223  11.00000  0.05    0.16
Q11   1   1.0006 -0.0478  0.6782  11.00000  0.05    0.16
Q12   1   1.1481  0.1299  0.6119  11.00000  0.05    0.15
Q13   1   0.9913  0.1509  0.7662  11.00000  0.05    0.15
Q14   1   1.3186 -0.0216  0.5046  11.00000  0.05    0.15
Q15   1   0.8162  0.2000  0.6497  11.00000  0.05    0.14
Q16   1   0.6518  0.3754  0.6402  11.00000  0.05    0.14
Q17   1   1.2797  0.0191  0.5427  11.00000  0.05    0.14
Q18   1   1.3130  0.1551  0.5480  11.00000  0.05    0.14
Q19   1   1.3336  0.0398  0.4992  11.00000  0.05    0.14
Q20   1   0.8358  0.3437  0.6308  11.00000  0.05    0.14
;
