#------------------------------------------------------------------------------
#$Date: 2015-07-05 12:16:56 +0300 (Sun, 05 Jul 2015) $
#$Revision: 140153 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/10/4031085.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_4031085
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 H6 N4 O8'
_chemical_formula_sum            'C4 H6 N4 O8'
_chemical_formula_weight         238.113
_chemical_name_common            '2,2-dinitropropyl nitrocarbamate'
_chemical_name_systematic        '2,2-dinitropropyl 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 Jul 30 17:24:56 2014'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.824(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4551(6)
_cell_length_b                   6.2566(2)
_cell_length_c                   9.7445(4)
_cell_measurement_reflns_used    2110
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.0400
_cell_measurement_theta_min      5.0920
_cell_volume                     906.55(6)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   23.00   95.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000  -30.0000 72

  2 omega   55.00   81.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   57.0000    0.0000 26

  3 omega   46.00   85.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000  -90.0000 39

  4 omega   15.00  103.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932   38.0000 -150.0000 88

  5 omega   25.00   74.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000  -30.0000 49

  6 omega   27.00   73.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       29.7932  -99.0000 -150.0000 46

  7 omega  -89.00  -34.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994 -179.0000  -60.0000 55

  8 omega -108.00  -32.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.6994  179.0000    0.0000 76

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      -0.0462781000
_diffrn_orient_matrix_UB_12      -0.0273561000
_diffrn_orient_matrix_UB_13      -0.0190560000
_diffrn_orient_matrix_UB_21      0.0096193000
_diffrn_orient_matrix_UB_22      -0.0882155000
_diffrn_orient_matrix_UB_23      0.0474695000
_diffrn_orient_matrix_UB_31      -0.0063573000
_diffrn_orient_matrix_UB_32      0.0658044000
_diffrn_orient_matrix_UB_33      0.0557348000
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_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            6513
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.19
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94255
_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    1.7446
_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          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.038
_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     169
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0312
_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)+(0.0351P)²+0.2302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                1574
_reflns_number_total             1849
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo5b00655_si_002.cif
_cod_data_source_block           3d
_cod_depositor_comments
'Adding full bibliography for 4031080--4031086.cif.'
_cod_database_code               4031085
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
H1 H 0.3897(12) 0.825(3) 0.2655(19) 0.041(5) Uiso 1 1 d
H2 H 0.4168(13) 0.731(3) 0.4208(19) 0.045(5) Uiso 1 1 d
H3 H 0.3194(12) 0.837(3) 0.3513(17) 0.036(4) Uiso 1 1 d
H4 H 0.2685(10) 0.644(2) 0.0725(16) 0.027(4) Uiso 1 1 d
H5 H 0.2344(10) 0.418(2) 0.0992(15) 0.025(4) Uiso 1 1 d
H6 H 0.0543(11) 0.760(3) 0.2422(18) 0.033(4) Uiso 1 1 d
C1 C 0.36803(11) 0.7518(3) 0.33473(17) 0.0304(3) Uani 1 1 d
C2 C 0.33122(9) 0.5407(2) 0.27202(13) 0.0216(3) Uani 1 1 d
C3 C 0.25298(9) 0.5545(2) 0.13862(14) 0.0238(3) Uani 1 1 d
C4 C 0.10617(9) 0.6855(2) 0.08578(13) 0.0218(3) Uani 1 1 d
N1 N 0.40667(8) 0.41466(19) 0.23732(12) 0.0283(3) Uani 1 1 d
N2 N 0.30137(8) 0.40019(18) 0.37968(12) 0.0258(3) Uani 1 1 d
N3 N 0.04329(8) 0.7517(2) 0.15352(13) 0.0268(3) Uani 1 1 d
N4 N -0.04418(7) 0.80605(18) 0.08282(12) 0.0255(3) Uani 1 1 d
O1 O 0.41132(7) 0.42129(18) 0.11552(10) 0.0358(3) Uani 1 1 d
O2 O 0.45925(8) 0.3243(3) 0.33544(13) 0.0598(4) Uani 1 1 d
O3 O 0.27533(8) 0.22204(16) 0.33883(12) 0.0373(3) Uani 1 1 d
O4 O 0.30368(8) 0.47569(18) 0.49542(10) 0.0393(3) Uani 1 1 d
O5 O 0.18198(6) 0.64807(15) 0.18839(9) 0.0239(2) Uani 1 1 d
O6 O 0.09683(7) 0.66328(17) -0.03906(9) 0.0305(2) Uani 1 1 d
O7 O -0.06741(7) 0.80391(18) -0.04622(10) 0.0354(3) Uani 1 1 d
O8 O -0.09003(7) 0.8528(2) 0.16060(11) 0.0421(3) 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
C2 C1 H1 107.5(11)
C2 C1 H2 110.6(10)
H1 C1 H2 109.7(15)
C2 C1 H3 109.1(10)
H1 C1 H3 107.1(14)
H2 C1 H3 112.6(14)
C1 C2 C3 115.09(12)
C1 C2 N1 108.57(11)
C3 C2 N1 108.63(10)
C1 C2 N2 112.18(11)
C3 C2 N2 107.49(10)
N1 C2 N2 104.30(10)
O5 C3 C2 103.72(10)
O5 C3 H4 110.6(9)
C2 C3 H4 109.3(10)
O5 C3 H5 109.2(9)
C2 C3 H5 112.2(9)
H4 C3 H5 111.6(13)
O6 C4 O5 125.42(12)
O6 C4 N3 128.15(12)
O5 C4 N3 106.43(10)
O1 N1 O2 125.69(12)
O1 N1 C2 117.07(11)
O2 N1 C2 117.15(11)
O4 N2 O3 125.77(12)
O4 N2 C2 118.32(11)
O3 N2 C2 115.88(11)
C4 N3 N4 123.82(11)
C4 N3 H6 122.9(11)
N4 N3 H6 113.3(11)
O8 N4 O7 126.65(12)
O8 N4 N3 114.13(11)
O7 N4 N3 119.22(11)
C4 O5 C3 114.35(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.501(2)
C1 H1 0.948(18)
C1 H2 0.972(19)
C1 H3 0.971(18)
C2 C3 1.5172(18)
C2 N1 1.5201(16)
C2 N2 1.5330(16)
C3 O5 1.4397(15)
C3 H4 0.933(15)
C3 H5 0.948(16)
C4 O6 1.1935(15)
C4 O5 1.3373(15)
C4 N3 1.3790(17)
N1 O1 1.2092(14)
N1 O2 1.2128(16)
N2 O4 1.2143(14)
N2 O3 1.2147(15)
N3 N4 1.3819(16)
N3 H6 0.836(16)
N4 O8 1.2062(15)
N4 O7 1.2100(14)
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 -66.09(14)
N1 C2 C3 O5 171.98(10)
N2 C2 C3 O5 59.68(13)
C1 C2 N1 O1 -97.29(14)
C3 C2 N1 O1 28.52(16)
N2 C2 N1 O1 142.94(12)
C1 C2 N1 O2 79.48(16)
C3 C2 N1 O2 -154.70(14)
N2 C2 N1 O2 -40.29(17)
C1 C2 N2 O4 5.42(16)
C3 C2 N2 O4 -122.07(13)
N1 C2 N2 O4 122.72(12)
C1 C2 N2 O3 -176.16(12)
C3 C2 N2 O3 56.36(14)
N1 C2 N2 O3 -58.85(14)
O6 C4 N3 N4 -0.4(2)
O5 C4 N3 N4 179.96(12)
C4 N3 N4 O8 177.53(13)
C4 N3 N4 O7 -2.8(2)
O6 C4 O5 C3 -6.13(19)
N3 C4 O5 C3 173.51(11)
C2 C3 O5 C4 176.92(11)
loop_
_iucr_refine_instructions_details
;
TITL P21c in P2(1)/c
CELL  0.71073  15.4551   6.2566   9.7445   90.000  105.824   90.000
ZERR     4.00   0.0006   0.0002   0.0004    0.000    0.004    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  16   24   16   32
MERG   2
SHEL  1000 0.8
FMAP   2
PLAN   20
ACTA
BOND   $H
CONF
L.S.   4
TEMP  -100.00
WGHT    0.035100    0.230200
FVAR       0.29238
H1    2    0.389713    0.824613    0.265453    11.00000    0.04124
H2    2    0.416847    0.730963    0.420763    11.00000    0.04453
H3    2    0.319412    0.837288    0.351321    11.00000    0.03636
H4    2    0.268542    0.644073    0.072549    11.00000    0.02673
H5    2    0.234448    0.417962    0.099173    11.00000    0.02476
H6    2    0.054323    0.760440    0.242175    11.00000    0.03276
MOLE    1
C1    1    0.368035    0.751811    0.334731    11.00000    0.02795    0.03040 =
         0.03261   -0.00282    0.00766   -0.00377
C2    1    0.331219    0.540689    0.272016    11.00000    0.02003    0.02457 =
         0.02107    0.00213    0.00721    0.00394
C3    1    0.252982    0.554458    0.138624    11.00000    0.02194    0.02984 =
         0.02050    0.00122    0.00703    0.00374
C4    1    0.106172    0.685513    0.085784    11.00000    0.02295    0.02094 =
         0.01959    0.00242    0.00273    0.00092
N1    3    0.406667    0.414662    0.237320    11.00000    0.02163    0.03395 =
         0.02910    0.00029    0.00672    0.00531
N2    3    0.301370    0.400188    0.379680    11.00000    0.02549    0.02690 =
         0.02541    0.00494    0.00765    0.00608
N3    3    0.043287    0.751741    0.153516    11.00000    0.02088    0.03884 =
         0.01814    0.00027    0.00105    0.00762
N4    3   -0.044180    0.806048    0.082821    11.00000    0.02169    0.02626 =
         0.02594    0.00022    0.00218    0.00213
O1    4    0.411322    0.421289    0.115518    11.00000    0.02981    0.05079 =
         0.02935   -0.00634    0.01233    0.00419
O2    4    0.459254    0.324256    0.335441    11.00000    0.04265    0.09484 =
         0.04288    0.02213    0.01331    0.04263
O3    4    0.275329    0.222040    0.338827    11.00000    0.04537    0.02424 =
         0.04332    0.00548    0.01392    0.00121
O4    4    0.303679    0.475692    0.495423    11.00000    0.05339    0.04458 =
         0.02339    0.00288    0.01623    0.00608
O5    4    0.181978    0.648065    0.188390    11.00000    0.01868    0.03367 =
         0.01831    0.00077    0.00324    0.00595
O6    4    0.096828    0.663285   -0.039064    11.00000    0.03086    0.04077 =
         0.01831    0.00119    0.00389    0.00694
O7    4   -0.067415    0.803906   -0.046222    11.00000    0.02891    0.04854 =
         0.02351    0.00238   -0.00196    0.00550
O8    4   -0.090026    0.852839    0.160597    11.00000    0.02680    0.06484 =
         0.03560   -0.00405    0.01014    0.01236
HKLF    4
 
REM  P21c in P2(1)/c
REM R1 =  0.0312 for   1574 Fo > 4sig(Fo)  and  0.0387 for all   1849 data
REM    169 parameters refined using      0 restraints
 
END
 
WGHT      0.0351      0.2302
REM Highest difference peak  0.230,  deepest hole -0.214,  1-sigma level  0.038
Q1    1   0.3206  0.4886  0.3182  11.00000  0.05    0.23
Q2    1   0.2969  0.5642  0.2110  11.00000  0.05    0.20
Q3    1   0.3588  0.4711  0.2480  11.00000  0.05    0.19
Q4    1   0.3458  0.6353  0.3003  11.00000  0.05    0.19
Q5    1   0.4685  0.4432  0.3138  11.00000  0.05    0.15
Q6    1   0.3630  0.5021  0.5002  11.00000  0.05    0.14
Q7    1   0.3946  0.3108  0.1458  11.00000  0.05    0.14
Q8    1   0.0628  0.6484  0.1192  11.00000  0.05    0.12
Q9    1   0.4255  0.2645  0.2643  11.00000  0.05    0.12
Q10   1   0.2157  0.6063  0.1589  11.00000  0.05    0.12
Q11   1   0.0779  0.7548  0.1240  11.00000  0.05    0.12
Q12   1   0.4802  0.3769  0.4530  11.00000  0.05    0.12
Q13   1   0.2407  0.2408  0.2489  11.00000  0.05    0.11
Q14   1   0.1473  0.6465  0.1365  11.00000  0.05    0.11
Q15   1   0.0003  0.7271  0.3436  11.00000  0.05    0.10
Q16   1   0.0388  0.6370 -0.0842  11.00000  0.05    0.10
Q17   1  -0.0775  0.8447  0.3136  11.00000  0.05    0.10
Q18   1   0.1823  0.6423  0.2236  11.00000  0.05    0.10
Q19   1   0.3184  0.2057  0.3386  11.00000  0.05    0.10
Q20   1   0.1463  0.5897 -0.0683  11.00000  0.05    0.10
;
