#------------------------------------------------------------------------------
#$Date: 2020-11-01 01:29:30 +0200 (Sun, 01 Nov 2020) $
#$Revision: 258666 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/94/1559438.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_1559438
loop_
_publ_author_name
'Unger, Cornelia C.'
'Holler, Marcel'
'Krumm, Burkhard'
'Klapötke, Thomas M.'
_publ_section_title
;
 Oxygen-Rich Bis(trinitroethyl esters): Suitable Oxidizers as Potential
 Ammonium Perchlorate Replacements
;
_journal_name_full               'Energy & Fuels'
_journal_paper_doi               10.1021/acs.energyfuels.0c02910
_journal_year                    2020
_chemical_formula_moiety         'C4 H6 N2 O6'
_chemical_formula_sum            'C4 H6 N2 O6'
_chemical_formula_weight         178.11
_chemical_name_common            N-ethyl-N-nitroglycine
_chemical_name_systematic        N-ethyl-N-nitroglycine
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date             2018-09-05
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8051(4)
_cell_length_b                   14.4941(7)
_cell_length_c                   5.2206(2)
_cell_measurement_reflns_used    1478
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.7420
_cell_measurement_theta_min      4.7320
_cell_volume                     666.26(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Microsoft Word 2016'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -3.00  99.00   1.00   15.00    --   29.79  77.00 -90.00  102
  2  ω     31.00  99.00   1.00   15.00    --   29.79  57.00 120.00   68
  3  ω     59.00  94.00   1.00   15.00    --   29.79 179.00 150.00   35
  4  ω   -104.00  27.00   1.00   15.00    --  -28.70   0.00 -60.00  131
  5  ω     26.00  95.00   1.00   15.00    --   29.79-133.00  39.00   69
  6  ω   -108.00 -60.00   1.00   15.00    --  -28.70-179.00  60.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0586045000
_diffrn_orient_matrix_UB_12      0.0137104000
_diffrn_orient_matrix_UB_13      -0.0850397000
_diffrn_orient_matrix_UB_21      0.0179701000
_diffrn_orient_matrix_UB_22      0.0469922000
_diffrn_orient_matrix_UB_23      0.0231620000
_diffrn_orient_matrix_UB_31      0.0521642000
_diffrn_orient_matrix_UB_32      -0.0007587000
_diffrn_orient_matrix_UB_33      -0.1034720000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4692
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         4.149
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     70
_refine_ls_number_reflns         709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0396P)²+0.1888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.000
_reflns_number_gt                603
_reflns_number_total             709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef0c02910_si_003.cif
_cod_data_source_block           nx345
_cod_database_code               1559438
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_res_file
;
TITL SIR92 run in space group P n m a
    shelx.res
    created by SHELXL-2018/3 at 15:23:57 on 20-Apr-2020
CELL  0.71073   8.8051  14.4941   5.2206   90.000   90.000   90.000
ZERR     4.00   0.0004   0.0007   0.0002    0.000    0.000    0.000
LATT   1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y, 1/2 - Z
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    N    O
UNIT  16 24 8 24
MERG   2
OMIT     0   3   1
OMIT     1   8   1
SHEL 1000   0.8
FMAP   2
PLAN   20
ACTA
BOND   $H
CONF
L.S.  25
TEMP  -150.00
WGHT    0.039600    0.188800
FVAR       0.83239
N2    3    0.968805    0.250000    0.434097    10.50000    0.01246    0.01440 =
         0.01809    0.00000   -0.00168    0.00000
N1    3    1.113640    0.250000    0.523491    10.50000    0.01405    0.01920 =
         0.01365    0.00000    0.00060    0.00000
O5    4    1.026840    0.112404    0.066312    11.00000    0.01973    0.01834 =
         0.01917   -0.00229    0.00260   -0.00180
O6    4    0.870786    0.015016    0.272525    11.00000    0.02737    0.01493 =
         0.02423   -0.00316    0.00490   -0.00365
O1    4    1.174880    0.174603    0.556829    11.00000    0.02004    0.02066 =
         0.02212    0.00336   -0.00122    0.00629
C2    1    0.938502    0.095066    0.238673    11.00000    0.01386    0.01652 =
         0.01685    0.00042   -0.00331    0.00024
C1    1    0.890381    0.162053    0.444275    11.00000    0.01615    0.01465 =
         0.01671    0.00177    0.00106   -0.00138
H1    2    0.783083    0.174683    0.423803    11.00000    0.01566
H2    2    0.907716    0.133088    0.610827    11.00000    0.01666
H3    2    0.901853   -0.022668    0.152225    11.00000    0.05420
HKLF    4




REM  SIR92 run in space group P n m a
REM wR2 = 0.0790, GooF = S = 1.076, Restrained GooF = 1.076 for all data
REM R1 = 0.0297 for 603 Fo > 4sig(Fo) and 0.0366 for all 709 data
REM 70 parameters refined using 0 restraints

END

WGHT      0.0396      0.1888

REM Highest difference peak  0.248,  deepest hole -0.230,  1-sigma level  0.046
Q1    1   0.9179  0.1307  0.3402  11.00000  0.05    0.25
Q2    1   1.0209  0.2500  0.4476  10.50000  0.05    0.22
Q3    1   0.9227  0.2036  0.4301  11.00000  0.05    0.17
Q4    1   1.0160  0.0889  0.2059  11.00000  0.05    0.17
Q5    1   0.9589  0.1439 -0.0779  11.00000  0.05    0.16
Q6    1   1.0237  0.2500  0.1250  10.50000  0.05    0.16
Q7    1   1.2915  0.1700  0.5680  11.00000  0.05    0.15
Q8    1   0.6182  0.2500  0.5420  10.50000  0.05    0.14
Q9    1   0.9707  0.2844  0.2927  11.00000  0.05    0.14
Q10   1   1.2675  0.1952  0.7094  11.00000  0.05    0.12
Q11   1   0.9268  0.1131  0.1034  11.00000  0.05    0.12
Q12   1   1.1253  0.1412 -0.0848  11.00000  0.05    0.11
Q13   1   0.9663  0.0415  0.0788  11.00000  0.05    0.11
Q14   1   0.7788  0.1836  0.2989  11.00000  0.05    0.11
Q15   1   0.6756  0.1862  0.2374  11.00000  0.05    0.11
Q16   1   1.1149  0.1110  0.1166  11.00000  0.05    0.11
Q17   1   0.9292  0.2500  0.0747  10.50000  0.05    0.11
Q18   1   1.0542  0.1622  0.4713  11.00000  0.05    0.11
Q19   1   1.0274  0.1736  0.0493  11.00000  0.05    0.10
Q20   1   1.0209  0.2500 -0.0624  10.50000  0.05    0.10
;
_shelx_res_checksum              63636
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.96881(16) 0.250000 0.4341(3) 0.0150(4) Uani 1 2 d S T P . .
N1 N 1.11364(16) 0.250000 0.5235(3) 0.0156(4) Uani 1 2 d S T P . .
O5 O 1.02684(10) 0.11240(7) 0.06631(17) 0.0191(3) Uani 1 1 d . . . . .
O6 O 0.87079(11) 0.01502(7) 0.2725(2) 0.0222(3) Uani 1 1 d . . . . .
O1 O 1.17488(11) 0.17460(6) 0.55683(18) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.93850(14) 0.09507(9) 0.2387(3) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.89038(15) 0.16205(9) 0.4443(3) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.7831(17) 0.1747(9) 0.424(3) 0.016(4) Uiso 1 1 d . . . . .
H2 H 0.9077(16) 0.1331(11) 0.611(3) 0.017(4) Uiso 1 1 d . . . . .
H3 H 0.902(2) -0.0227(16) 0.152(5) 0.054(6) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0125(8) 0.0144(8) 0.0181(8) 0.000 -0.0017(6) 0.000
N1 0.0140(7) 0.0192(9) 0.0136(8) 0.000 0.0006(6) 0.000
O5 0.0197(5) 0.0183(5) 0.0192(5) -0.0023(4) 0.0026(4) -0.0018(4)
O6 0.0274(6) 0.0149(5) 0.0242(5) -0.0032(4) 0.0049(4) -0.0036(4)
O1 0.0200(5) 0.0207(5) 0.0221(5) 0.0034(4) -0.0012(4) 0.0063(4)
C2 0.0139(6) 0.0165(7) 0.0168(6) 0.0004(5) -0.0033(5) 0.0002(5)
C1 0.0161(7) 0.0146(7) 0.0167(7) 0.0018(5) 0.0011(5) -0.0014(5)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 C1 115.75(8) . 8_565 ?
N1 N2 C1 115.75(8) . . ?
C1 N2 C1 122.97(14) 8_565 . ?
O1 N1 O1 125.19(15) 8_565 . ?
O1 N1 N2 117.39(7) 8_565 . ?
O1 N1 N2 117.38(7) . . ?
C2 O6 H3 108.2(15) . . ?
O5 C2 O6 124.85(12) . . ?
O5 C2 C1 124.99(12) . . ?
O6 C2 C1 110.16(11) . . ?
N2 C1 C2 113.95(11) . . ?
N2 C1 H1 107.1(8) . . ?
C2 C1 H1 108.5(8) . . ?
N2 C1 H2 109.6(9) . . ?
C2 C1 H2 108.2(9) . . ?
H1 C1 H2 109.4(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 N1 1.358(2) . ?
N2 C1 1.4507(14) 8_565 ?
N2 C1 1.4507(14) . ?
N1 O1 1.2310(11) . ?
O5 C2 1.2157(16) . ?
O6 C2 1.3164(16) . ?
O6 H3 0.88(2) . ?
C2 C1 1.5081(19) . ?
C1 H1 0.968(15) . ?
C1 H2 0.978(16) . ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
? ? ? ? ? ? ? ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N1 O1 -13.8(2) 8_565 . . 8_565 ?
C1 N2 N1 O1 -168.45(13) . . . 8_565 ?
C1 N2 N1 O1 168.45(13) 8_565 . . . ?
C1 N2 N1 O1 13.8(2) . . . . ?
N1 N2 C1 C2 -76.26(17) . . . . ?
C1 N2 C1 C2 131.16(13) 8_565 . . . ?
O5 C2 C1 N2 -4.77(19) . . . . ?
O6 C2 C1 N2 175.33(11) . . . . ?
